Kinetic resolution of propargylic alcohols catalyzed by benzotetramisole

被引：108

作者：

Birman, Vladimir B. ^{[1
]}

Guo, Lei ^{[1
]}

机构：

[1] Washington Univ, Dept Chem, St Louis, MO 63130 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 21期

关键词：

D O I：

10.1021/ol061906y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Kinetic resolution of variously substituted secondary propargylic alcohols catalyzed by benzotetramisole (BTM) proceeds with selectivity factors up to 32, the highest ever achieved with nonenzymatic catalysts for this class of substrates.

引用

页码：4859 / 4861

页数：3

共 25 条

[1] The kinetic resolution of allylic alcohols by a non-enzymatic acylation catalyst; application to natural product synthesis
Bellemin-Laponnaz, S
Tweddell, J
Ruble, JC
Breitling, FM
Fu, GC
[J]. CHEMICAL COMMUNICATIONS, 2000, (12) : 1009 - 1010
[2] Benzotetramisole: A remarkably enantioselective acyl transfer catalyst
Birman, VB
Li, XM
[J]. ORGANIC LETTERS, 2006, 8 (07) : 1351 - 1354
[3] Kinetic resolution of alcohols using a 1,2-dihydroimidazo[1,2-a]quinoline enantioselective acylation catalyst
Birman, VB
Jiang, H
[J]. ORGANIC LETTERS, 2005, 7 (16) : 3445 - 3447
[4] 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
[5] Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation
Birman, Vladimir B.
Jiang, Hui
Li, Ximin
Guo, Lei
Uffman, Eric W.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (20) : 6536 - 6537
[6] SELECTIVE REDUCTIONS .46. EFFECT OF THE STERIC REQUIREMENT AT THE 2-POSITION OF APOPINENE ON CHIRAL REDUCTIONS - B-(ISO-2-ETHYLAPOPINOCAMPHEYL)-9-BORABICYCLO[3.3.1]NONANES AND B-(ISO-2-N-PROPYLAPOPINOCAMPHEYL)-9-BORABICYCLO[3.3.1]NONANES AS IMPROVED REAGENTS FOR THE CHIRAL REDUCTION OF ALPHA,BETA-ACETYLENIC KETONES AND ALPHA-KETO ESTERS
BROWN, HC
RAMACHANDRAN, PV
WEISSMAN, SA
SWAMINATHAN, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (26) : 6328 - 6333
[7] ENANTIOSELECTIVE ESTERIFICATIONS OF UNSATURATED ALCOHOLS MEDIATED BY A LIPASE PREPARED FROM PSEUDOMONAS SP
BURGESS, K
JENNINGS, LD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 6129 - 6139
[8] In the golden age of organocatalysis
Dalko, PI
Moisan, L
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) : 5138 - 5175
[9] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine
Fu, GC
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) : 542 - 547
[10] JARVO ER, 2004, COMPREHENSIVE ASYM S, V1, pCH43

← 1 2 3 →