一种由（-）-鹰爪豆碱导向的硼脯氨酸的高度对映选择性合成。固态和溶液态结构及性质。

A (-)-sparteine-directed highly enantioselective synthesis of boroproline. Solid- and solution-state structure and properties.

作者信息

Batsanov Andrei S, Grosjean Christophe, Schütz Thorben, Whiting Andrew

机构信息

Chemistry Department, Durham University, Science Laboratories, South Road, Durham, U.K.

出版信息

J Org Chem. 2007 Aug 3;72(16):6276-9. doi: 10.1021/jo0708792. Epub 2007 Jul 12.

DOI:10.1021/jo0708792

PMID:17628110

Abstract

A two-step, direct asymmetric synthesis of the trifluoroacetate ammonium salt of boroproline is reported. (-)-Sparteine-mediated lithiation of N-Boc-pyrrolidine afforded N-Boc-aminoboronic acid in good yield and enantioselectivity as determined by HPLC (pinanediol ester). Deprotection using TFA yielded the ammonium salt; full characterization data are presented, and the structure in aqueous solution and the occurrence of a B-N species are discussed.

摘要

报道了硼脯氨酸三氟乙酸铵盐的两步直接不对称合成。（-）-司巴丁介导的N-Boc-吡咯烷锂化反应以良好的产率和对映选择性得到了N-Boc-氨基硼酸（通过HPLC（蒎烷二醇酯）测定）。使用三氟乙酸进行脱保护得到铵盐；给出了完整的表征数据，并讨论了其在水溶液中的结构以及B-N物种的存在情况。