STEREOSELECTIVE SYNTHESIS OF ALCOHOLS .34. TOWARDS AN UNDERSTANDING OF CRAM ANTI-CRAM SELECTIVITY ON ADDITION OF CROTYLBORONATES TO ALPHA-METHYLBUTYRALDEHYDE

被引：35

作者：

HOFFMANN, RW

BRINKMANN, H

FRENKING, G

机构：

[1] Fachbereich Chemie der Philipps-Universität, Marburg, D-3550, Hans‐Meerwein‐Straße, Lahn

来源：

CHEMISCHE BERICHTE | 1990年 / 123卷 / 12期

关键词：

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

D O I：

10.1002/cber.19901231222

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The diastereoselectivity on addition of gamma-substituted allylboronates to apha-methylbutyraldehyde (9) did not depend on the size of the substituent in the reagent, but only on its location in the Z or E position. This finding required a reinterpretation of the reasons for the attendant reversal in diastereoselectivity. New hypotheses are presented based on force-field calculations on model structures for the transition states.

引用

收藏

页码：2387 / 2394

页数：8

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