Nonlinear effects in the reduction of acetophenone by diisopinocampheyl chloroborane: influence of the stoichiometry of the reagent

被引：15

作者：

Girard, C ^{[1
]}

Kagan, HB ^{[1
]}

机构：

[1] Univ Paris 11, CNRS, Lab React Organ Select, F-91405 Orsay, France

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 23期

关键词：

D O I：

10.1016/S0957-4166(97)00592-2

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A nonlinear effect (NLE) between the ees of diisopinocampheyl chloroborane (ee(aux)) and the ees of 1-phenylethanol (ee(prod)) has previously been observed during the reduction of acetophenone. The size of this asymmetric amplification is related to the amount of Ipc(2)BCl used to perform the reduction, as we report in this communication. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

引用

页码：3851 / 3854

页数：4

共 17 条

[1] HYDROBORATION OF TERPENES .9. A SIMPLE IMPROVED PROCEDURE FOR UPGRADING THE OPTICAL PURITY OF COMMERCIALLY AVAILABLE ALPHA-PINENES AND BETA-PINENES - CONVERSION OF (+)-ALPHA-PINENE TO (+)-BETA-PINENE VIA HYDROBORATION ISOMERIZATION
BROWN, HC
JOSHI, NN
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (17) : 4059 - 4062
[2] DEVELOPMENT OF A SIMPLE GENERAL PROCEDURE FOR SYNTHESIS OF PURE ENANTIOMERS VIA CHIRAL ORGANOBORANES
BROWN, HC
SINGARAM, B
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (08) : 287 - 293
[3] HYDROBORATION .18. REACTION OF DIISOPINOCAMPHEYLBORANE WITH REPRESENTATIVE CIS-ACYCLIC CYCLIC + BICYCLIC OLEFINS . CONVENIENT SYNTHESIS OF OPTICALLY ACTIVE ALCOHOLS + OLEFINS OF HIGH OPTICAL PURITY + ESTABLISHED CONFIGURATION
BROWN, HC
AYYANGAR, NR
ZWEIFEL, G
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (03) : 397 - &
[4] CHIRAL SYNTHESIS VIA ORGANOBORANES .6. HYDROBORATION .74. ASYMMETRIC HYDROBORATION OF REPRESENTATIVE HETEROCYCLIC OLEFINS WITH DIISOPINOCAMPHEYLBORANE - SYNTHESIS OF HETEROCYCLIC BORONATES AND HETEROCYCLIC ALCOHOLS OF VERY HIGH ENANTIOMERIC PURITY
BROWN, HC
PRASAD, JVNV
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) : 2049 - 2054
[5] BROWN HC, 1961, J AM CHEM SOC, V83, P486, DOI 10.1021/ja01463a054
[6] HYDROBORATION .62. MONOISOPINOCAMPHEYLBORANE, AN EXCELLENT CHIRAL HYDROBORATING AGENT FOR TRANS-DISUBSTITUTED AND TRISUBSTITUTED ALKENES - EVIDENCE FOR A STRONG STERIC DEPENDENCE IN SUCH ASYMMETRIC HYDROBORATIONS
BROWN, HC
JADHAV, PK
MANDAL, AK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (26) : 5074 - 5083
[7] BROWN HC, 1982, J ORG CHEM, V47, P4059
[8] Chandrasekharan J., 1985, J ORG CHEM, V50, P5448
[9] NONLINEAR EFFECTS IN THE REDUCTION OF ACETOPHENONE BY DIISOPINOCAMPHENYL CHLOROBORANE - INFLUENCE OF THE REAGENT PREPARATION
GIRARD, C
KAGAN, HB
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (08) : 1881 - 1884
[10] NONLINEAR EFFECTS IN ASYMMETRIC CATALYSIS
GUILLANEUX, D
ZHAO, SH
SAMUEL, O
RAINFORD, D
KAGAN, HB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (21) : 9430 - 9439

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