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Showing 1 to 12 of 196 entries
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Tetraarylphosphonium Salt-Catalyzed Synthesis of Oxazolidinones from Isocyanates and Epoxides.

Organic letters

Toda Y, Gomyou S, Tanaka S, Komiyama Y, Kikuchi A, Suga H.
PMID: 29039956
Org Lett. 2017 Nov 03;19(21):5786-5789. doi: 10.1021/acs.orglett.7b02722.

Preparation of a range of oxazolidinones, including enantioenriched N-aryl-substituted oxazolidinones, in which tetraarylphosphonium salts (TAPS) catalyze the [3 + 2] coupling reaction of isocyanates and epoxides effectively, is described. The key finding is a Brønsted acid/halide ion bifunctional catalyst...

Asymmetric solution-phase mixture aldol reaction using oligomeric ethylene glycol tagged chiral oxazolidinones.

Tetrahedron letters

Turkyilmaz S, Wilcox CS.
PMID: 29056780
Tetrahedron Lett. 2017 May 24;58(21):2031-2033. doi: 10.1016/j.tetlet.2017.04.026. Epub 2017 Apr 06.

Sorting tags are oligomeric structures that can be used as protecting groups or chiral auxiliaries enabling solution-phase mixture syntheses of multiple tagged compounds in one pot and allowing for facile and predictable chromatographic separation of products at the end...

Diastereoselective synthesis of tetrahydrofurans by Lewis acid catalyzed intermolecular carbenoid-carbonyl reaction-cycloaddition sequences: unusual diastereoselectivity of Lewis acid catalyzed cycloadditions.

The Journal of organic chemistry

Hashimoto Y, Itoh K, Kakehi A, Shiro M, Suga H.
PMID: 23758193
J Org Chem. 2013 Jun 21;78(12):6182-95. doi: 10.1021/jo400858u. Epub 2013 Jun 12.

The effects of including metal salts for three-component reactions involving α-alkyl-α-diazo esters, aromatic aldehydes, and 3-(2-alkenoyl)-2-oxazolidinones are described, in terms of yields and diastereoselectivities. Metal tetrafluoroborates (10-30 mol %) such as Co(BF4)2·6H2O, Ni(BF4)2·6H2O, and AgBF4 were effective in delivering...

Reliable (13)C NMR Method of Making Relative Stereochemical Assignments to Certain N-[alpha-Hetero-beta-hydroxy(acetoxy)-beta-(substituted phenyl)-1'-oxopropyl]-2-oxazolidinones.

The Journal of organic chemistry

Pridgen LN, De Brosse C.
PMID: 11671387
J Org Chem. 1997 Jan 10;62(1):216-220. doi: 10.1021/jo951798l.

No abstract available.

Synthesis of Vicinal Amino Alcohols via a Tandem Acylnitrene Aziridination-Aziridine Ring Opening.

The Journal of organic chemistry

Bergmeier SC, Stanchina DM.
PMID: 11671773
J Org Chem. 1997 Jun 27;62(13):4449-4456. doi: 10.1021/jo970473x.

A facile synthesis of differently substituted vicinal amino alcohols is reported. We have demonstrated that these amino alcohols could be readily prepared from the oxazolidinones by treatment with aqueous base. We have synthesized a variety of substituted bicyclic aziridine...

Synthesis of 2-oxazolidinones by direct palladium-catalyzed oxidative carbonylation of 2-amino-1-alkanols.

Organic letters

Gabriele B, Salerno G, Brindisi D, Costa M, Chiusoli GP.
PMID: 10814394
Org Lett. 2000 Mar 09;2(5):625-7. doi: 10.1021/ol9913789.

[reaction: see text] 2-Oxazolidinones 2 are obtained in excellent yields (up to 100%) and with unprecedented catalytic efficiencies (up to 2000 mol of product/mol of catalyst used) by direct PdI2/KI-catalyzed oxidative carbonylation of the readily available 2-amino-1-alkanols 1. Reactions...

Unprecedented effects of achiral oxazolidinones on enantioselective radical-mediated conjugate additions using a chiral zinc triflate.

Organic letters

Murakata M, Tsutsui H, Hoshino O.
PMID: 11430059
Org Lett. 2001 Jan 25;3(2):299-302. doi: 10.1021/ol006927l.

[figure: see text] A role of achiral oxazolidinones to enhance the enantioselectivity in reactions of N-cinnamoyloxazolidinones with alkyl radicals promoted by a chiral Lewis acid is described. Efficient enantioselective radical-mediated conjugate additions of N-cinnamoyloxazolidinone can be realized by use...

Intramolecular iron(II)-catalyzed nitrogen transfer reactions of unsaturated alkoxycarbonyl azides: a facile and stereoselective route to 4,5-disubstituted oxazolidinones.

Chemistry (Weinheim an der Bergstrasse, Germany)

Bach T, Schlummer B, Harms K.
PMID: 11465449
Chemistry. 2001 Jun 18;7(12):2581-94. doi: 10.1002/1521-3765(20010618)7:12<2581::aid-chem25810>3.0.co;2-o.

Intramolecular FeII-catalyzed reactions of various unsaturated alkoxycarbonyl azides are described. The reactions occur in the presence of stoichiometric amounts of trimethyl silyl chloride employing ethanol as the solvent. The corresponding 2-alkenyloxycarbonyl azides 5, 9, 18, 20, 22, and 24...

Catalytic asymmetric direct alpha-amination reactions of 2-keto esters: a simple synthetic approach to optically active syn-beta-amino-alpha-hydroxy esters.

Journal of the American Chemical Society

Juhl K, Jørgensen KA.
PMID: 11890774
J Am Chem Soc. 2002 Mar 20;124(11):2420-1. doi: 10.1021/ja0175486.

The catalytic enantioselective direct alpha-amination reaction of 2-keto esters with easily available azo dicarboxylates as the nitrogen source and chiral bisoxazoline-copper(II) complexes as the catalyst is presented. The reactions proceed with excellent enantioselectivities and high yields. The scope of...

Palladium(II)-catalyzed highly regio- and diastereoselective cyclization of difunctional allylic N-tosylcarbamates. A convenient synthesis of optically active 4-vinyl-2-oxazolidinones and total synthesis of 1,4-dideoxy-1,4-imino-L-xylitol.

The Journal of organic chemistry

Lei A, Liu G, Lu X.
PMID: 11856047
J Org Chem. 2002 Feb 08;67(3):974-80. doi: 10.1021/jo0161429.

A Pd(II)-catalyzed cyclization of difunctional allylic N-tosyl carbamates in the presence of halide ions was developed with high regio- and diastereoselectivity. The reaction involves aminopalladation of alkene and beta-heteroatom elimination to regenerate Pd(II) species. When the readily available homochiral...

Dicationic [(BINAP)Pd(solvent)2]2+[TfO-]2: enantioselective hydroamination catalyst for alkenoyl-N-oxazolidinones.

Chemical communications (Cambridge, England)

Li K, Hii KK.
PMID: 12778702
Chem Commun (Camb). 2003 May 21;(10):1132-3. doi: 10.1039/b302246c.

Dicationic (BINAP)palladium(II) complex induced high enantioselectiviies in the addition of primary (and secondary) aromatic amines to alpha,beta-unsaturated oxazolidinones (up to 93% ee).

Asymmetric 1,3-dipolar cycloaddition reactions of nitrile oxides catalyzed by chiral binaphthyldiimine-Ni(II) complexes.

The Journal of organic chemistry

Suga H, Adachi Y, Fujimoto K, Furihata Y, Tsuchida T, Kakehi A, Baba T.
PMID: 19093832
J Org Chem. 2009 Feb 06;74(3):1099-113. doi: 10.1021/jo802392c.

Asymmetric cycloaddition reactions between several nitrile oxides and 3-(2-alkenoyl)-2-oxazolidinones and 2-(2-alkenoyl)-3-pyrazolidinone derivatives were carried out in the presence of chiral binaphthyldiimine (BINIM)-Ni(II) complexes as catalysts. Using (R)-BINIM-4(3,5-xylyl)-2QN-Ni(II) complex (30 mol %), good regioselectivity (4-Me/5-Me = 85:15) along with high...

Showing 1 to 12 of 196 entries