STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .35. ADDITION OF E-CROTYLBORONATES AND Z-CROTYLBORONATES TO CHIRAL ALPHA-SUBSTITUTED ALDEHYDES

被引：44

作者：

BRINKMANN, H ^{[1
]}

HOFFMANN, RW ^{[1
]}

机构：

[1] UNIV MARBURG,FACHBEREICH CHEM,HANS MEERWEIN STR,W-3550 MARBURG,GERMANY

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 12期

关键词：

ALLYLBORATION REACTION; ASYMMETRIC INDUCTION; CALCULATIONS; FORCE-FIELD; TRANSITION-STATE MODELS;

D O I：

10.1002/cber.19901231223

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direction (Cram/anti-Cram) and the extent of asymmetric induction on addition of crotylboronates to a range of chiral aldehydes was investigated. A reversal in the sense of the asymmetric induction on changing from the Z- to the E-crotylboronate was found for aldehydes having polar-alpha-substituents and for some of the nonpolar chiral aldehydes. Force-field calculations on transition-state models reproduced these results in the majority of the cases investigated despite of unaccounted short comings of the method.

引用

页码：2395 / 2401

页数：7

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