β-（羟烷基）-γ-丁内酯的有机催化对映选择性合成

Organocatalytic and enantioselective synthesis of beta-(hydroxyalkyl)-gamma-butyrolactones.

作者信息

Hajra Saumen, Giri Aswini Kumar

机构信息

Department of Chemistry, Indian Institute of Technology, Kharagpur, India.

出版信息

J Org Chem. 2008 May 16;73(10):3935-7. doi: 10.1021/jo8005733. Epub 2008 Apr 9.

DOI:10.1021/jo8005733

PMID:18396909

Abstract

Organocatalytic cross-aldol reaction of methyl 4-oxobutyrate (2) and a variety of aldehydes 3 followed by reduction with NaBH(4) has provided a one-pot, general and efficient method for the synthesis of 4-(hydroxyalkyl)-gamma-butyrolactones 1 with high diastereo-(dr > 24:1) and enantioselectivity (ee > 99%).

摘要

4-氧代丁酸甲酯（2）与多种醛（3）的有机催化交叉羟醛反应，随后用硼氢化钠（NaBH₄）还原，提供了一种一锅法、通用且高效的合成4-（羟烷基）-γ-丁内酯（1）的方法，具有高非对映选择性（dr > 24:1）和对映选择性（ee > 99%）。