A general strategy for improving enantiomeric purities via the tandem use of mirror-image catalysts

被引:17
作者
Faller, JW [1 ]
Lavoie, AR [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
关键词
D O I
10.1021/om010960+
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In situations where the asymmetric transfer hydrogenation catalysis of a given ketone gives moderate, though insufficiently high ee, the enantiomeric purity of the resulting alcohol can be enhanced via a subsequent asymmetric dehydrogenation with the antipode of the catalyst. Herein, we report on the theoretical and experimental aspects of this strategy.
引用
收藏
页码:2010 / 2012
页数:3
相关论文
共 35 条
[11]  
Girard C, 1998, ANGEW CHEM INT EDIT, V37, P2923, DOI 10.1002/(SICI)1521-3773(19981116)37:21<2922::AID-ANIE2922>3.0.CO
[12]  
2-1
[13]   The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones [J].
Haack, KJ ;
Hashiguchi, S ;
Fujii, A ;
Ikariya, T ;
Noyori, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :285-288
[14]   METHOD FOR OBTAINING AN ENANTIOMER CONTAINING LESS THAN 0.1 PERCENT OF ITS ANTIPODE - DETERMINATION OF ITS MAXIMUM ROTATORY POWER [J].
HOREAU, A .
TETRAHEDRON, 1975, 31 (10) :1307-1309
[15]   Nonlinear effects in kinetic resolutions [J].
Johnson, DW ;
Singleton, DA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9307-9312
[16]  
Kagan H.B., 2007, TOPICS STEREOCHEMIST, V18, P249, DOI 10.1002/9780470147276.ch4
[17]  
Keith JM, 2001, ADV SYNTH CATAL, V343, P5, DOI 10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO
[18]  
2-I
[19]   Kinetic resolution when the chiral auxiliary is not enantiomerically pure: Normal and abnormal behavior [J].
Luukas, TO ;
Girard, C ;
Fenwick, DR ;
Kagan, HB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9299-9306
[20]   KINETIC RESOLUTION OF RACEMIC ALLYLIC ALCOHOLS BY ENANTIOSELECTIVE EPOXIDATION - A ROUTE TO SUBSTANCES OF ABSOLUTE ENANTIOMERIC PURITY [J].
MARTIN, VS ;
WOODARD, SS ;
KATSUKI, T ;
YAMADA, Y ;
IKEDA, M ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (20) :6237-6240