通过脯氨酸催化的连续 α-氨氧化/α-氨基化和醛的 Horner-Wadsworth-Emmons 烯烃化反应对映选择性合成 syn/anti-1,3-氨基醇。

Enantioselective synthesis of syn/anti-1,3-amino alcohols via proline-catalyzed sequential alpha-aminoxylation/alpha-amination and Horner-Wadsworth-Emmons olefination of aldehydes.

机构信息

Division of Organic Chemistry, National Chemical Laboratory, Pune 411 008, India.

出版信息

Org Lett. 2010 Jun 18;12(12):2762-5. doi: 10.1021/ol100856u.

PMID:20476722

Abstract

A novel and general method for asymmetric synthesis of both syn/anti-1,3-amino alcohols is described. The method uses proline-catalyzed sequential alpha-aminoxylation/ alpha-amination and Horner-Wadsworth-Emmons (HWE) olefination of aldehydes as the key step. By using this method, a short synthesis of a bioactive molecule, (R)-1-((S)-1-methylpyrrolidin-2-yl)-5-phenylpentan-2-ol, is also accomplished.

摘要

本文描述了一种新型且通用的手性合成 syn/anti-1,3-氨基醇的方法。该方法以脯氨酸催化的醛的连续α-氨氧化/α-氨基化和 Horner-Wadsworth-Emmons（HWE）烯烃化为关键步骤。通过使用该方法，还实现了生物活性分子 (R)-1-((S)-1-甲基吡咯烷-2-基)-5-苯基戊烷-2-醇的短合成。