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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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