Planar chiral hydroxy derivatives of [2.2]paracyclophane as auxiliaries for asymmetric allylboration

被引：0
作者：
N. V. Vorontsova
R. P. Zhuravsky
E. V. Sergeeva
E. V. Vorontsov
Z. A. Starikova
V. I. Rozenberg
机构：
[1] Russian Academy of Sciences,A. N. Nesmeyanov Institute of Organoelement Compounds
来源：
Russian Chemical Bulletin | 2007年 / 56卷
关键词：
[2.2]paracyclophanes; allylboration; asymmetric synthesis; planar chirality; chiral auxiliaries; homoallylic alcohols; X-ray diffraction study;
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摘要：
Allylboronic esters with various structures were synthesized for the first time based on [2.2]paracyclophane derivatives containing one or two hydroxy groups. It was demonstrated that these esters can be used as chiral inductors in the asymmetric allylboration of benzaldehyde. The highest enantiomeric excess of 1-phenylbut-3-en-1-ol (60%) was achieved in the reactions with acyclic bis-O,O′-(paracyclophanyl) allylboronates based on (S)-4-hydroxy-and (S)-12-bromo-4-hydroxy[2.2]paracyclophanes. (S)-4-Hydroxy[2.2]paracyclophane was studied by X-ray diffraction.
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页码：2225 / 2231
页数：6
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