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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 41期

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

页码：12098 / 12099

页数：2

共 24 条

[1] Hydroborations catalysed by transition metal complexes
Beletskaya, I
Pelter, A
[J]. TETRAHEDRON, 1997, 53 (14) : 4957 - 5026
[2] TRANSITION-METAL-PROMOTED HYDROBORATIONS OF ALKENES, EMERGING METHODOLOGY FOR ORGANIC TRANSFORMATIONS
BURGESS, K
OHLMEYER, MJ
[J]. CHEMICAL REVIEWS, 1991, 91 (06) : 1179 - 1191
[3] REACTIONS OF CATECHOLBORANE WITH WILKINSON CATALYST - IMPLICATIONS FOR TRANSITION METAL-CATALYZED HYDROBORATIONS OF ALKENES
BURGESS, K
VANDERDONK, WA
WESTCOTT, SA
MARDER, TB
BAKER, RT
CALABRESE, JC
[J]. 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
DORIGO, AE
SCHLEYER, PV
[J]. 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
EVANS, DA
FU, GC
ANDERSON, BA
[J]. 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
EVANS, DA
FU, GC
HOVEYDA, AH
[J]. 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
EVANS, DA
FU, GC
HOVEYDA, AH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) : 6917 - 6918
[10] Hayashi T., 1999, COMPREHENSIVE ASYMME, V1, P351

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