Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline

被引:47
作者
Terakado, D [1 ]
Koutaka, H [1 ]
Oriyama, T [1 ]
机构
[1] Ibaraki Univ, Fac Sci, Ibaraki 3108512, Japan
关键词
D O I
10.1016/j.tetasy.2005.01.034
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A highly efficient and good enantioselective organocatalytic asymmetric acylation of racemic primary alcohols with acyl chlorides has been achieved catalyzed by a chiral 1,2-diamine derived from (S)-proline. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1157 / 1165
页数:9
相关论文
共 47 条
[1]   The kinetic resolution of allylic alcohols by a non-enzymatic acylation catalyst; application to natural product synthesis [J].
Bellemin-Laponnaz, S ;
Tweddell, J ;
Ruble, JC ;
Breitling, FM ;
Fu, GC .
CHEMICAL COMMUNICATIONS, 2000, (12) :1009-1010
[2]   Formation of scalemic aziridines via the nucleophilic opening of aziridines [J].
Bergmeier, SC ;
Seth, PP .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2671-2674
[3]  
CHARETTE AB, 2004, ORG SYNTH COLL, V10, P613
[4]   GENERAL-ASPECTS AND OPTIMIZATION OF ENANTIOSELECTIVE BIOCATALYSIS IN ORGANIC-SOLVENTS - THE USE OF LIPASES [J].
CHEN, CS ;
SIH, CJ .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (06) :695-707
[5]   QUANTITATIVE-ANALYSES OF BIOCHEMICAL KINETIC RESOLUTIONS OF ENANTIOMERS [J].
CHEN, CS ;
FUJIMOTO, Y ;
GIRDAUKAS, G ;
SIH, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (25) :7294-7299
[6]   Minimal acylase-like peptides. Conformational control of absolute stereospecificity [J].
Copeland, GT ;
Jarvo, ER ;
Miller, SJ .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (20) :6784-6785
[7]   Enantioselective nucleophilic catalysis with "planar-chiral" heterocycles [J].
Fu, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (06) :412-420
[8]   Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine [J].
Fu, GC .
ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :542-547
[9]   CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION [J].
GAO, Y ;
HANSON, RM ;
KLUNDER, JM ;
KO, SY ;
MASAMUNE, H ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) :5765-5780
[10]   Nucleophilic catalysis with π-bound nitrogen heterocycles:: Synthesis of the first ruthenium catalysts and comparison of the reactivity and the enantioselectivity of ruthenium and iron complexes [J].
Garrett, CE ;
Fu, GC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) :7479-7483