Reversal of enantioselectivity in the asymmetric rhodium- versus iridium-catalyzed hydroboration of meso substrates

被引:77
作者
Luna, AP
Bonin, M
Micouin, L
Husson, HP
机构
[1] CNRS, UMR 8638, Chim Therapeut Lab, F-75270 Paris 06, France
[2] Univ Paris 05, Fac Sci Pharmaceut & Biol, F-75270 Paris, France
关键词
D O I
10.1021/ja026714m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Ir-catalyzed asymmetric hydroboration of bicyclic hydrazines with ee and chemical yields up to 64% is reported. The switch from rhodium to iridium leads systematically to opposite enantiomers in this desymmetrization reaction. Copyright © 2002 American Chemical Society.
引用
收藏
页码:12098 / 12099
页数:2
相关论文
共 24 条
[1]   Hydroborations catalysed by transition metal complexes [J].
Beletskaya, I ;
Pelter, A .
TETRAHEDRON, 1997, 53 (14) :4957-5026
[2]   TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS [J].
BURGESS, K ;
OHLMEYER, MJ .
CHEMICAL REVIEWS, 1991, 91 (06) :1179-1191
[3]   REACTIONS OF CATECHOLBORANE WITH WILKINSON CATALYST - IMPLICATIONS FOR TRANSITION METAL-CATALYZED HYDROBORATIONS OF ALKENES [J].
BURGESS, K ;
VANDERDONK, WA ;
WESTCOTT, SA ;
MARDER, TB ;
BAKER, RT ;
CALABRESE, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (24) :9350-9359
[4]  
Consiglio G, 2001, CHIMIA, V55, P809
[5]   AN AB-INITIO INVESTIGATION OF THE RH-I-CATALYZED HYDROBORATION OF C=C BONDS - EVIDENCE FOR HYDROGEN MIGRATION IN THE KEY STEP [J].
DORIGO, AE ;
SCHLEYER, PV .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (01) :115-118
[6]  
DORIGO AE, 1995, ANGEW CHEM, V107, P108
[7]   MECHANISTIC STUDY OF THE RHODIUM(I)-CATALYZED HYDROBORATION REACTION [J].
EVANS, DA ;
FU, GC ;
ANDERSON, BA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6679-6685
[8]   RHODIUM(I)-CATALYZED AND IRIDIUM(I)-CATALYZED HYDROBORATION REACTIONS - SCOPE AND SYNTHETIC APPLICATIONS [J].
EVANS, DA ;
FU, GC ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (17) :6671-6679
[9]   RHODIUM(I)-CATALYZED HYDROBORATION OF OLEFINS - THE DOCUMENTATION OF REGIOCHEMICAL AND STEREOCHEMICAL CONTROL IN CYCLIC AND ACYCLIC SYSTEMS [J].
EVANS, DA ;
FU, GC ;
HOVEYDA, AH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6917-6918
[10]  
Hayashi T., 1999, COMPREHENSIVE ASYMME, V1, P351