Enantioselective acylation of secondary alcohols catalyzed by chiral N-heterocyclic carbenes

被引：180

作者：

Kano, T ^{[1
]}

Sasaki, K ^{[1
]}

Maruoka, K ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 07期

关键词：

D O I：

10.1021/ol050174r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthetic utility of chiral N-heterocyclic carbenes, which have been used mainly in transition metal-catalyzed reactions as a ligand, was demonstrated by the enantioselective acylation of secondary alcohols.

引用

页码：1347 / 1349

页数：3

共 50 条

[1] Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition
Alexakis, A
Winn, CL
Guillen, F
Pytkowicz, J
Roland, S
Mangeney, P
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) : 345 - 348
[2] 2,3-dihydroimidazo[1,2-a]pyridines: A new class of enantioselective acyl transfer catalysts and their use in kinetic resolution of alcohols
Birman, VB
Uffman, EW
Hui, J
Li, XM
Kilbane, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (39) : 12226 - 12227
[3] Organocatalyzed conjugate umpolung of α,β-unsaturated aldehydes for the synthesis of γ-butyrolactones
Burstein, C
Glorius, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (45) : 6205 - 6208
[4] Catalytic generation of activated carboxylates:: Direct, stereoselective synthesis of β-hydroxyesters from epoxyaldehydes
Chow, KYK
Bode, JW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (26) : 8126 - 8127
[5] First example of N-heterocyclic carbenes as catalysts for living polymerization:: Organocatalytic ring-opening polymerization of cyclic esters
Connor, EF
Nyce, GW
Myers, M
Möck, A
Hedrick, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) : 914 - 915
[6] Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope
Copeland, GT
Miller, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (27) : 6496 - 6502
[7] Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO
[8] 2-D
[9] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
[10] Catalysis of benzoin condensation by conformationally-restricted chiral bicyclic thiazolium salts
Dvorak, CA
Rawal, VH
[J]. TETRAHEDRON LETTERS, 1998, 39 (19) : 2925 - 2928

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