聚合物负载手性催化剂催化环戊二烯与甲基丙烯的不对称Diels-Alder反应

Reactive Polymers Pub Date : 1995-02-01 DOI:10.1016/0923-1137(94)00087-L

Shinichi Itsuno, Katsuhiro Watanabe, Takahiro Koizumi, Koichi Ito

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引用次数: 24

摘要

用溴硼烷和具有手性氨基醇或二醇基团的交联聚合物制备了手性路易斯酸。这些聚合物作为手性催化剂用于环戊二烯与甲基丙烯的Diels-Alder反应，得到了高收率、高外显选择性的光学活性环加合物。采用以(S)-脯氨酸为原料的高分子手性催化剂，获得了高达54% ee的光收率。讨论了这种方法在不对称合成中的应用前景。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Asymmetric Diels-Alder reaction of cyclopentadiene with methacrolein using polymer-supported chiral catalysts

Polymer-supported chiral Lewis acids were prepared from bromoboranes and crosslinked polymers having chiral amino alcohol or diol moieties. These polymers were used as chiral catalysts for Diels-Alder reactions of cyclopentadiene with methacrolein to give optically active cycloadduct in high chemical yield with high exo selectivity. Optical yield up to 54% ee was obtained by the use of polymeric chiral catalyst derived from (S)-proline. The potential of this type of approach in asymmetric synthesis is discussed.

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