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One-Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions.

Chemistry (Weinheim an der Bergstrasse, Germany)

Gelozia S, Kwon Y, McDonald R, West FG.
PMID: 29444379
Chemistry. 2018 Apr 20;24(23):6052-6056. doi: 10.1002/chem.201800758. Epub 2018 Mar 26.

Organoaluminum-mediated double interrupted Nazarov cyclization to access bicyclo[3.1.0]hexanols via nucleophilic methyl attack followed by Simmons-Smith-type electrophilic cyclopropanation is reported. These alcohols can undergo ring opening to afford cyclohexanones or cyclohexenones, broadening the range of scaffolds available via interrupted Nazarov...

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Gelozia S, Kwon Y, McDonald R, et al. One-Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions. Chemistry. 2018;24(23):6052-6056doi: 10.1002/chem.201800758.
Gelozia, S., Kwon, Y., McDonald, R., & West, F. G. (2018). One-Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions. Chemistry (Weinheim an der Bergstrasse, Germany), 24(23), 6052-6056. https://doi.org/10.1002/chem.201800758
Gelozia, Shorena, et al. "One-Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 24,23 (2018): 6052-6056. doi: https://doi.org/10.1002/chem.201800758
Gelozia S, Kwon Y, McDonald R, West FG. One-Pot Generation of Bicyclo[3.1.0]hexanols and Cyclohexanones by Double Interrupted Nazarov Reactions. Chemistry. 2018 Apr 20;24(23):6052-6056. doi: 10.1002/chem.201800758. Epub 2018 Mar 26. PMID: 29444379.
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Synthesis of novel 2-azabicyclo[2.2.0]- and [2.1.1]hexanols.

The Journal of organic chemistry

Krow GR, Lester WS, Liu N, Yuan J, Hiller A, Duo J, Herzon SB, Nguyen Y, Cannon K.
PMID: 11262132
J Org Chem. 2001 Mar 09;66(5):1811-7. doi: 10.1021/jo001558s.

Methyl- and phenyl-substituted N-(ethoxycarbonyl)-2-azabicyclo[2.2.0]hex-5-enes 6 were reacted with NBS in wet DMSO to afford bromohydrins. Mixtures of unrearranged 6-exo-bromo-5-endo-hydroxy-2-azabicyclo[2.2.0]hexanes 7a,b and rearranged 5-anti-bromo-6-anti-hydroxy-2-azabicyclo[2.1.1]hexanes 8a,b were formed stereoselectively from the parent alkene 6a and 4-methyl alkene 6b. The 5-methyl alkene...

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Krow GR, Lester WS, Liu N, et al. Synthesis of novel 2-azabicyclo[2.2.0]- and [2.1.1]hexanols. J Org Chem. 2001;66(5):1811-7doi: 10.1021/jo001558s.
Krow, G. R., Lester, W. S., Liu, N., Yuan, J., Hiller, A., Duo, J., Herzon, S. B., Nguyen, Y., & Cannon, K. (2001). Synthesis of novel 2-azabicyclo[2.2.0]- and [2.1.1]hexanols. The Journal of organic chemistry, 66(5), 1811-7. https://doi.org/10.1021/jo001558s
Krow, G R, et al. "Synthesis of novel 2-azabicyclo[2.2.0]- and [2.1.1]hexanols." The Journal of organic chemistry vol. 66,5 (2001): 1811-7. doi: https://doi.org/10.1021/jo001558s
Krow GR, Lester WS, Liu N, Yuan J, Hiller A, Duo J, Herzon SB, Nguyen Y, Cannon K. Synthesis of novel 2-azabicyclo[2.2.0]- and [2.1.1]hexanols. J Org Chem. 2001 Mar 09;66(5):1811-7. doi: 10.1021/jo001558s. PMID: 11262132.
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Highly Enantio- and Diastereoselective Synthesis of 2-Substituted 1-Bicyclo[3.1.0]hexanols.

Angewandte Chemie (International ed. in English)

Mizojiri R, Urabe H, Sato F.
PMID: 29711618
Angew Chem Int Ed Engl. 1998 Oct 16;37(19):2666-2668. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2666::AID-ANIE2666>3.0.CO;2-K.

Useful intermediates in organic synthesis, optically active bicyclic cyclopropanols were difficult to prepare by existing methods. They can now be readily synthesized with high enantio- and diastereoselectivity from Oppolzer's N-acylcamphorsultams and [Ti(OiPr)

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Mizojiri R, Urabe H, Sato F. Highly Enantio- and Diastereoselective Synthesis of 2-Substituted 1-Bicyclo[3.1.0]hexanols. Angew Chem Int Ed Engl. 1998;37(19):2666-2668doi: 10.1002/(SICI)1521-3773(19981016)37:19<2666::AID-ANIE2666>3.0.CO;2-K.
Mizojiri, R., Urabe, H., & Sato, F. (1998). Highly Enantio- and Diastereoselective Synthesis of 2-Substituted 1-Bicyclo[3.1.0]hexanols. Angewandte Chemie (International ed. in English), 37(19), 2666-2668. https://doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2666::AID-ANIE2666>3.0.CO;2-K
Mizojiri, Ryo, et al. "Highly Enantio- and Diastereoselective Synthesis of 2-Substituted 1-Bicyclo[3.1.0]hexanols." Angewandte Chemie (International ed. in English) vol. 37,19 (1998): 2666-2668. doi: https://doi.org/10.1002/(SICI)1521-3773(19981016)37:19<2666::AID-ANIE2666>3.0.CO;2-K
Mizojiri R, Urabe H, Sato F. Highly Enantio- and Diastereoselective Synthesis of 2-Substituted 1-Bicyclo[3.1.0]hexanols. Angew Chem Int Ed Engl. 1998 Oct 16;37(19):2666-2668. doi: 10.1002/(SICI)1521-3773(19981016)37:19<2666::AID-ANIE2666>3.0.CO;2-K. PMID: 29711618.
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Thermodynamic and Dynamic Properties of Micellar Aggregates of Nonionic Surfactants with Short Hydrophobic Tails.

Journal of colloid and interface science

Ambrosone L, Costantino L, D'errico G, Vitagliano V.
PMID: 9241168
J Colloid Interface Sci. 1997 Jun 15;190(2):286-93. doi: 10.1006/jcis.1997.4860.

The densities and viscosities of binary aqueous mixtures of poly(ethylenoxide)hexanols [C6 H13 (OCH2 CH2 )m OH, C6 Em ] (m = 3, 4, and 5) have been studied in the micellar composition range. For the same surfactants the self-diffusion...

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Ambrosone L, Costantino L, D'errico G, et al. Thermodynamic and Dynamic Properties of Micellar Aggregates of Nonionic Surfactants with Short Hydrophobic Tails. J Colloid Interface Sci. 1997;190(2):286-93doi: 10.1006/jcis.1997.4860.
Ambrosone, L., Costantino, L., D'errico, G., & Vitagliano, V. (1997). Thermodynamic and Dynamic Properties of Micellar Aggregates of Nonionic Surfactants with Short Hydrophobic Tails. Journal of colloid and interface science, 190(2), 286-93. https://doi.org/10.1006/jcis.1997.4860
Ambrosone, et al. "Thermodynamic and Dynamic Properties of Micellar Aggregates of Nonionic Surfactants with Short Hydrophobic Tails." Journal of colloid and interface science vol. 190,2 (1997): 286-93. doi: https://doi.org/10.1006/jcis.1997.4860
Ambrosone L, Costantino L, D'errico G, Vitagliano V. Thermodynamic and Dynamic Properties of Micellar Aggregates of Nonionic Surfactants with Short Hydrophobic Tails. J Colloid Interface Sci. 1997 Jun 15;190(2):286-93. doi: 10.1006/jcis.1997.4860. PMID: 9241168.
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Stereoisomers and analogs of 14-methyl-1-octadecene, sex pheromone of peach leafminer moth,Lyonetia clerkella, L.

Journal of chemical ecology

Sonnet PE, Proveaux AT, Adamek E, Sugie H, Sato R, Tamaki Y.
PMID: 24301893
J Chem Ecol. 1987 Mar;13(3):547-55. doi: 10.1007/BF01880098.

The synthesis of the enantiomeric 14-methyl-1-octadecenes in >99% EE is described. Enantiomeric 2-methyl-1-hexanols were intermediates in the synthesis. The 1-alkene had been previously identified as the sex pheromone of the peach leafminer moth. Several closely related structures that have...

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Sonnet PE, Proveaux AT, Adamek E, et al. Stereoisomers and analogs of 14-methyl-1-octadecene, sex pheromone of peach leafminer moth,Lyonetia clerkella, L. J Chem Ecol. 1987;13(3):547-55doi: 10.1007/BF01880098.
Sonnet, P. E., Proveaux, A. T., Adamek, E., Sugie, H., Sato, R., & Tamaki, Y. (1987). Stereoisomers and analogs of 14-methyl-1-octadecene, sex pheromone of peach leafminer moth,Lyonetia clerkella, L. Journal of chemical ecology, 13(3), 547-55. https://doi.org/10.1007/BF01880098
Sonnet, P E, et al. "Stereoisomers and analogs of 14-methyl-1-octadecene, sex pheromone of peach leafminer moth,Lyonetia clerkella, L." Journal of chemical ecology vol. 13,3 (1987): 547-55. doi: https://doi.org/10.1007/BF01880098
Sonnet PE, Proveaux AT, Adamek E, Sugie H, Sato R, Tamaki Y. Stereoisomers and analogs of 14-methyl-1-octadecene, sex pheromone of peach leafminer moth,Lyonetia clerkella, L. J Chem Ecol. 1987 Mar;13(3):547-55. doi: 10.1007/BF01880098. PMID: 24301893.
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A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method.

The Journal of organic chemistry

Weckerle B, Schreier P, Humpf HU.
PMID: 11722220
J Org Chem. 2001 Nov 30;66(24):8160-4. doi: 10.1021/jo010768h.

A new one-step strategy is described for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method. Using the 9-anthroate chromophore for the derivatization of both functional groups, the resulting bisignate CD curves unequivocally allow...

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Weckerle B, Schreier P, Humpf HU. A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method. J Org Chem. 2001;66(24):8160-4doi: 10.1021/jo010768h.
Weckerle, B., Schreier, P., & Humpf, H. U. (2001). A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method. The Journal of organic chemistry, 66(24), 8160-4. https://doi.org/10.1021/jo010768h
Weckerle, B, et al. "A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method." The Journal of organic chemistry vol. 66,24 (2001): 8160-4. doi: https://doi.org/10.1021/jo010768h
Weckerle B, Schreier P, Humpf HU. A new one-step strategy for the stereochemical assignment of acyclic 2- and 3-sulfanyl-1-alkanols using the CD exciton chirality method. J Org Chem. 2001 Nov 30;66(24):8160-4. doi: 10.1021/jo010768h. PMID: 11722220.
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Showing 1 to 6 of 6 entries