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Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation.

The Journal of organic chemistry

Guyon H, Boussonnière A, Castanet AS.
PMID: 28394126
J Org Chem. 2017 May 05;82(9):4949-4957. doi: 10.1021/acs.joc.7b00423. Epub 2017 Apr 21.

A new class of chiral 1,2-amino ether ligands, readily accessible from naturally occurring α-amino- or α-hydroxy acids, was found to provide high levels of both conversion and stereocontrol (up to 95:5 er) in intramolecular carbolithiation reactions, outperforming the benchmark...

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Guyon H, Boussonnière A, Castanet AS. Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation. J Org Chem. 2017;82(9):4949-4957doi: 10.1021/acs.joc.7b00423.
Guyon, H., Boussonnière, A., & Castanet, A. S. (2017). Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation. The Journal of organic chemistry, 82(9), 4949-4957. https://doi.org/10.1021/acs.joc.7b00423
Guyon, Hélène, et al. "Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation." The Journal of organic chemistry vol. 82,9 (2017): 4949-4957. doi: https://doi.org/10.1021/acs.joc.7b00423
Guyon H, Boussonnière A, Castanet AS. Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation. J Org Chem. 2017 May 05;82(9):4949-4957. doi: 10.1021/acs.joc.7b00423. Epub 2017 Apr 21. PMID: 28394126.
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The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Scharnagel D, Müller A, Prause F, Eck M, Goller J, Milius W, Breuning M.
PMID: 26230668
Chemistry. 2015 Aug 24;21(35):12488-500. doi: 10.1002/chem.201502090. Epub 2015 Jul 31.

The first modular and flexible synthesis of core-chiral bispidines was achieved by using an "inside-out" strategy. The key intermediate, a NBoc-activated bispidine lactam, was constructed in enantiomerically pure form from a chirally modified β-amino acid and 2-(acetoxymethyl)acrylonitrile in just...

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Scharnagel D, Müller A, Prause F, et al. The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions. Chemistry. 2015;21(35):12488-500doi: 10.1002/chem.201502090.
Scharnagel, D., Müller, A., Prause, F., Eck, M., Goller, J., Milius, W., & Breuning, M. (2015). The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 21(35), 12488-500. https://doi.org/10.1002/chem.201502090
Scharnagel, Dagmar, et al. "The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 21,35 (2015): 12488-500. doi: https://doi.org/10.1002/chem.201502090
Scharnagel D, Müller A, Prause F, Eck M, Goller J, Milius W, Breuning M. The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions. Chemistry. 2015 Aug 24;21(35):12488-500. doi: 10.1002/chem.201502090. Epub 2015 Jul 31. PMID: 26230668.
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Medicine: Anhelonium Lewinii-Glenard's Disease, or Enteroptosis-Sparteine Sulphate and Chloroform-Uræmic Dyspnœa-Chloride of Ammonium in Delirium Tremens-Electro Diagnosis and Electro-Therapeutics Simplified -Salol in Diarrhœa.

The Indian medical gazette

Moir DM.
PMID: 29002803
Ind Med Gaz. 1897 Feb;32(2):71-73.

No abstract available.

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Moir DM. Medicine: Anhelonium Lewinii-Glenard's Disease, or Enteroptosis-Sparteine Sulphate and Chloroform-Uræmic Dyspnœa-Chloride of Ammonium in Delirium Tremens-Electro Diagnosis and Electro-Therapeutics Simplified -Salol in Diarrhœa. Ind Med Gaz. 1897;32(2):71-73
Moir, D. M. (1897). Medicine: Anhelonium Lewinii-Glenard's Disease, or Enteroptosis-Sparteine Sulphate and Chloroform-Uræmic Dyspnœa-Chloride of Ammonium in Delirium Tremens-Electro Diagnosis and Electro-Therapeutics Simplified -Salol in Diarrhœa. The Indian medical gazette, 32(2), 71-73.
Moir, D M. "Medicine: Anhelonium Lewinii-Glenard's Disease, or Enteroptosis-Sparteine Sulphate and Chloroform-Uræmic Dyspnœa-Chloride of Ammonium in Delirium Tremens-Electro Diagnosis and Electro-Therapeutics Simplified -Salol in Diarrhœa." The Indian medical gazette vol. 32,2 (1897): 71-73.
Moir DM. Medicine: Anhelonium Lewinii-Glenard's Disease, or Enteroptosis-Sparteine Sulphate and Chloroform-Uræmic Dyspnœa-Chloride of Ammonium in Delirium Tremens-Electro Diagnosis and Electro-Therapeutics Simplified -Salol in Diarrhœa. Ind Med Gaz. 1897 Feb;32(2):71-73. PMID: 29002803; PMCID: PMC5148354.
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Exploring stereogenic phosphorus: synthetic strategies for diphosphines containing bulky, highly symmetric substituents.

The Journal of organic chemistry

Maienza F, Spindler F, Thommen M, Pugin B, Malan C, Mezzetti A.
PMID: 12126412
J Org Chem. 2002 Jul 26;67(15):5239-49. doi: 10.1021/jo020130l.

Diphosphine ligands bearing highly symmetric, bulky substituents at a stereogenic P atom were prepared, exploiting established protocols, which include the use of chiral synthons such as 3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine-2-borane (3a) and phenylmethylchlorophosphine borane (10) and the enantioselective deprotonation of dimethylarylphosphine boranes....

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Maienza F, Spindler F, Thommen M, et al. Exploring stereogenic phosphorus: synthetic strategies for diphosphines containing bulky, highly symmetric substituents. J Org Chem. 2002;67(15):5239-49doi: 10.1021/jo020130l.
Maienza, F., Spindler, F., Thommen, M., Pugin, B., Malan, C., & Mezzetti, A. (2002). Exploring stereogenic phosphorus: synthetic strategies for diphosphines containing bulky, highly symmetric substituents. The Journal of organic chemistry, 67(15), 5239-49. https://doi.org/10.1021/jo020130l
Maienza, Francesca, et al. "Exploring stereogenic phosphorus: synthetic strategies for diphosphines containing bulky, highly symmetric substituents." The Journal of organic chemistry vol. 67,15 (2002): 5239-49. doi: https://doi.org/10.1021/jo020130l
Maienza F, Spindler F, Thommen M, Pugin B, Malan C, Mezzetti A. Exploring stereogenic phosphorus: synthetic strategies for diphosphines containing bulky, highly symmetric substituents. J Org Chem. 2002 Jul 26;67(15):5239-49. doi: 10.1021/jo020130l. PMID: 12126412.
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Asymmetric Syntheses of Derivatives of beta- and gamma-Aryl and alpha-Alkyl Amino Acids Using n-BuLi/(-)-Sparteine.

The Journal of organic chemistry

Kim BJ, Park YS, Beak P.
PMID: 11674240
J Org Chem. 1999 Mar 05;64(5):1705-1708. doi: 10.1021/jo9817568.

No abstract available.

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Kim BJ, Park YS, Beak P. Asymmetric Syntheses of Derivatives of beta- and gamma-Aryl and alpha-Alkyl Amino Acids Using n-BuLi/(-)-Sparteine. J Org Chem. 1999;64(5):1705-1708doi: 10.1021/jo9817568.
Kim, B. J., Park, Y. S., & Beak, P. (1999). Asymmetric Syntheses of Derivatives of beta- and gamma-Aryl and alpha-Alkyl Amino Acids Using n-BuLi/(-)-Sparteine. The Journal of organic chemistry, 64(5), 1705-1708. https://doi.org/10.1021/jo9817568
Kim, Bong Jin, et al. "Asymmetric Syntheses of Derivatives of beta- and gamma-Aryl and alpha-Alkyl Amino Acids Using n-BuLi/(-)-Sparteine." The Journal of organic chemistry vol. 64,5 (1999): 1705-1708. doi: https://doi.org/10.1021/jo9817568
Kim BJ, Park YS, Beak P. Asymmetric Syntheses of Derivatives of beta- and gamma-Aryl and alpha-Alkyl Amino Acids Using n-BuLi/(-)-Sparteine. J Org Chem. 1999 Mar 05;64(5):1705-1708. doi: 10.1021/jo9817568. PMID: 11674240.
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(-)-Sparteine-mediated metalation of ferrocenesulfonates. The first case of double asymmetric induction of ferrocene planar chirality.

Organic letters

Metallinos C, Snieckus V.
PMID: 12027651
Org Lett. 2002 May 30;4(11):1935-8. doi: 10.1021/ol025963c.

[reaction: see text] A new process for induction of planar chirality via a matched chiral-directed metalation group (DMG)/(-)-sparteine interaction is demonstrated. Thus, s-BuLi metalation of (-)-menthylferrocenesulfonate (8b) with (-)-sparteine constitutes a matched pair resulting in amplification of the dr...

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Metallinos C, Snieckus V. (-)-Sparteine-mediated metalation of ferrocenesulfonates. The first case of double asymmetric induction of ferrocene planar chirality. Org Lett. 2002;4(11):1935-8doi: 10.1021/ol025963c.
Metallinos, C., & Snieckus, V. (2002). (-)-Sparteine-mediated metalation of ferrocenesulfonates. The first case of double asymmetric induction of ferrocene planar chirality. Organic letters, 4(11), 1935-8. https://doi.org/10.1021/ol025963c
Metallinos, Costa, and Snieckus, Victor. "(-)-Sparteine-mediated metalation of ferrocenesulfonates. The first case of double asymmetric induction of ferrocene planar chirality." Organic letters vol. 4,11 (2002): 1935-8. doi: https://doi.org/10.1021/ol025963c
Metallinos C, Snieckus V. (-)-Sparteine-mediated metalation of ferrocenesulfonates. The first case of double asymmetric induction of ferrocene planar chirality. Org Lett. 2002 May 30;4(11):1935-8. doi: 10.1021/ol025963c. PMID: 12027651.
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Synthesis of an ethynyl carbamate and application for enantioselective cyclocarbolithiation.

Organic letters

Gralla G, Wibbeling B, Hoppe D.
PMID: 12074665
Org Lett. 2002 Jun 27;4(13):2193-5. doi: 10.1021/ol0260674.

[reaction: see text] The intramolecular trans-cyclocarbolithiation of the alpha-lithiated 4-substituted 5-hexynyl carbamate (1S,4RS)-14 employing lithiodestannylation is presented. The 5-exo-dig cyclization products cis-/trans-16a were formed exclusively. The highly enantioenriched organotin precursor (S)-11 was synthesized via an asymmetric deprotonation of the...

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Gralla G, Wibbeling B, Hoppe D. Synthesis of an ethynyl carbamate and application for enantioselective cyclocarbolithiation. Org Lett. 2002;4(13):2193-5doi: 10.1021/ol0260674.
Gralla, G., Wibbeling, B., & Hoppe, D. (2002). Synthesis of an ethynyl carbamate and application for enantioselective cyclocarbolithiation. Organic letters, 4(13), 2193-5. https://doi.org/10.1021/ol0260674
Gralla, Gabriele, et al. "Synthesis of an ethynyl carbamate and application for enantioselective cyclocarbolithiation." Organic letters vol. 4,13 (2002): 2193-5. doi: https://doi.org/10.1021/ol0260674
Gralla G, Wibbeling B, Hoppe D. Synthesis of an ethynyl carbamate and application for enantioselective cyclocarbolithiation. Org Lett. 2002 Jun 27;4(13):2193-5. doi: 10.1021/ol0260674. PMID: 12074665.
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[tBuLi.(-)-sparteine]: molecular structure of the first monomeric butyllithium compound.

Angewandte Chemie (International ed. in English)

Strohmann C, Seibel T, Strohfeldt K.
PMID: 14520758
Angew Chem Int Ed Engl. 2003 Sep 29;42(37):4531-3. doi: 10.1002/anie.200351308.

No abstract available.

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Strohmann C, Seibel T, Strohfeldt K. [tBuLi.(-)-sparteine]: molecular structure of the first monomeric butyllithium compound. Angew Chem Int Ed Engl. 2003;42(37):4531-3doi: 10.1002/anie.200351308.
Strohmann, C., Seibel, T., & Strohfeldt, K. (2003). [tBuLi.(-)-sparteine]: molecular structure of the first monomeric butyllithium compound. Angewandte Chemie (International ed. in English), 42(37), 4531-3. https://doi.org/10.1002/anie.200351308
Strohmann, Carsten, et al. "[tBuLi.(-)-sparteine]: molecular structure of the first monomeric butyllithium compound." Angewandte Chemie (International ed. in English) vol. 42,37 (2003): 4531-3. doi: https://doi.org/10.1002/anie.200351308
Strohmann C, Seibel T, Strohfeldt K. [tBuLi.(-)-sparteine]: molecular structure of the first monomeric butyllithium compound. Angew Chem Int Ed Engl. 2003 Sep 29;42(37):4531-3. doi: 10.1002/anie.200351308. PMID: 14520758.
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Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols.

Organic & biomolecular chemistry

Hodgson DM, Stent MA, Stefane B, Wilson FX.
PMID: 12926388
Org Biomol Chem. 2003 Apr 07;1(7):1139-50. doi: 10.1039/b212404a.

A screen of external chiral ligands has led to enantioselective organolithium-induced alkylative double ring-opening of 3,4-epoxytetrahydrofuran 1 with n-BuLi to give 3-methyleneheptane-1,2-diol 3 in 75% yield and 55% ee in the presence of bisoxazoline 10, and in up to...

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Hodgson DM, Stent MA, Stefane B, et al. Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols. Org Biomol Chem. 2003;1(7):1139-50doi: 10.1039/b212404a.
Hodgson, D. M., Stent, M. A., Stefane, B., & Wilson, F. X. (2003). Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols. Organic & biomolecular chemistry, 1(7), 1139-50. https://doi.org/10.1039/b212404a
Hodgson, David M, et al. "Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols." Organic & biomolecular chemistry vol. 1,7 (2003): 1139-50. doi: https://doi.org/10.1039/b212404a
Hodgson DM, Stent MA, Stefane B, Wilson FX. Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols. Org Biomol Chem. 2003 Apr 07;1(7):1139-50. doi: 10.1039/b212404a. PMID: 12926388.
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Highly enantioenriched homoenolate reagents by asymmetric gamma-deprotonation of achiral 1-silyl-substituted 1-alkenyl carbamates.

Organic letters

Reuber J, Fröhlich R, Hoppe D.
PMID: 14986974
Org Lett. 2004 Mar 04;6(5):783-6. doi: 10.1021/ol0364677.

1-trimethylsilyl-1-alkenyl carbamates 1 are deprotonated by n-butyllithium/(-)-sparteine (2) with a high degree of enantiotopic differentiation in the gamma-position to form the enantiomerically enriched allyllithium derivatives 3. Trapping these with several electrophiles proceeds stereospecifically in an anti-S(E)' or syn-S(E)' substitution...

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Reuber J, Fröhlich R, Hoppe D. Highly enantioenriched homoenolate reagents by asymmetric gamma-deprotonation of achiral 1-silyl-substituted 1-alkenyl carbamates. Org Lett. 2004;6(5):783-6doi: 10.1021/ol0364677.
Reuber, J., Fröhlich, R., & Hoppe, D. (2004). Highly enantioenriched homoenolate reagents by asymmetric gamma-deprotonation of achiral 1-silyl-substituted 1-alkenyl carbamates. Organic letters, 6(5), 783-6. https://doi.org/10.1021/ol0364677
Reuber, Jenny, et al. "Highly enantioenriched homoenolate reagents by asymmetric gamma-deprotonation of achiral 1-silyl-substituted 1-alkenyl carbamates." Organic letters vol. 6,5 (2004): 783-6. doi: https://doi.org/10.1021/ol0364677
Reuber J, Fröhlich R, Hoppe D. Highly enantioenriched homoenolate reagents by asymmetric gamma-deprotonation of achiral 1-silyl-substituted 1-alkenyl carbamates. Org Lett. 2004 Mar 04;6(5):783-6. doi: 10.1021/ol0364677. PMID: 14986974.
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Effects of Coumarin and Sparteine on Attachment to Cellulose and Cellulolysis by Neocallimastix frontalis RE1.

Applied and environmental microbiology

Moniello G, Richardson AJ, Duncan SH, Stewart CS.
PMID: 16535476
Appl Environ Microbiol. 1996 Dec;62(12):4666-8. doi: 10.1128/aem.62.12.4666-4668.1996.

The plant secondary metabolites coumarin and sparteine reduced attachment to cellulose, cellulose solubilization, and the proportion of lactate in the fermentation products of the anaerobic fungus Neocallimastix frontalis RE1. Neither compound directly inhibited the endoglucanase or lactate dehydrogenase activities...

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Moniello G, Richardson AJ, Duncan SH, et al. Effects of Coumarin and Sparteine on Attachment to Cellulose and Cellulolysis by Neocallimastix frontalis RE1. Appl Environ Microbiol. 1996;62(12):4666-8doi: 10.1128/aem.62.12.4666-4668.1996.
Moniello, G., Richardson, A. J., Duncan, S. H., & Stewart, C. S. (1996). Effects of Coumarin and Sparteine on Attachment to Cellulose and Cellulolysis by Neocallimastix frontalis RE1. Applied and environmental microbiology, 62(12), 4666-8. https://doi.org/10.1128/aem.62.12.4666-4668.1996
Moniello, G, et al. "Effects of Coumarin and Sparteine on Attachment to Cellulose and Cellulolysis by Neocallimastix frontalis RE1." Applied and environmental microbiology vol. 62,12 (1996): 4666-8. doi: https://doi.org/10.1128/aem.62.12.4666-4668.1996
Moniello G, Richardson AJ, Duncan SH, Stewart CS. Effects of Coumarin and Sparteine on Attachment to Cellulose and Cellulolysis by Neocallimastix frontalis RE1. Appl Environ Microbiol. 1996 Dec;62(12):4666-8. doi: 10.1128/aem.62.12.4666-4668.1996. PMID: 16535476; PMCID: PMC1389014.
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Catalytic asymmetric deprotonation using a ligand exchange approach.

Journal of the American Chemical Society

McGrath MJ, O'Brien P.
PMID: 16305208
J Am Chem Soc. 2005 Nov 30;127(47):16378-9. doi: 10.1021/ja056026d.

A novel ligand exchange approach to catalytic asymmetric deprotonation-electrophilic trapping has been developed that uses 1.3 equiv of s-BuLi, 0.06-0.2 equiv of chiral diamine ((-)-sparteine or a (+)-sparteine surrogate), and 1.2 equiv of achiral bispidine. The methodology is illustrated...

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McGrath MJ, O'Brien P. Catalytic asymmetric deprotonation using a ligand exchange approach. J Am Chem Soc. 2005;127(47):16378-9doi: 10.1021/ja056026d.
McGrath, M. J., & O'Brien, P. (2005). Catalytic asymmetric deprotonation using a ligand exchange approach. Journal of the American Chemical Society, 127(47), 16378-9. https://doi.org/10.1021/ja056026d
McGrath, Matthew J, and O'Brien, Peter. "Catalytic asymmetric deprotonation using a ligand exchange approach." Journal of the American Chemical Society vol. 127,47 (2005): 16378-9. doi: https://doi.org/10.1021/ja056026d
McGrath MJ, O'Brien P. Catalytic asymmetric deprotonation using a ligand exchange approach. J Am Chem Soc. 2005 Nov 30;127(47):16378-9. doi: 10.1021/ja056026d. PMID: 16305208.
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Showing 1 to 12 of 120 entries