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通过微波辐射和氮杂环丙烷-2-甲醇催化剂加速芳基锌的形成及其对醛的对映选择性加成反应。

Acceleration of arylzinc formation and its enantioselective addition to aldehydes by microwave irradiation and aziridine-2-methanol catalysts.

作者信息

Braga Antonio L, Paixão Marcio W, Westermann Bernhard, Schneider Paulo H, Wessjohann Ludger A

机构信息

Universidade Federal de Santa Maria, Departamento de Química, 97105-900, Santa Maria RS, Brazil.

出版信息

J Org Chem. 2008 Apr 4;73(7):2879-82. doi: 10.1021/jo702413n. Epub 2008 Mar 4.

DOI:10.1021/jo702413n
PMID:18315002
Abstract

The formation and 2-amino alcohol catalyzed addition of arylzinc reagents from and with boronic acids, respectively, is drastically accelerated to a few minutes under microwave irradiation without loss of enantioselectivity (up to 98% ee). Of the amino acid derived catalysts tested, the conformationally restricted bulky substituted aziridine-2-methanols derived from serine show the best overall performance in the formation of diarylmethanols.

摘要

在微波辐射下，芳基锌试剂分别与硼酸形成以及2-氨基醇催化的芳基锌试剂与硼酸的加成反应，能在几分钟内大幅加速，且对映选择性不会降低（高达98% ee）。在所测试的氨基酸衍生催化剂中，源自丝氨酸的构象受限的大位阻取代氮杂环丙烷-2-甲醇在二芳基甲醇的形成中表现出最佳的整体性能。

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