通过对映体纯的乙烯基恶唑烷衍生物的铃木交叉偶联反应合成非天然氨基酸。

Synthesis of unnatural amino acids via Suzuki cross-coupling of enantiopure vinyloxazolidine derivatives.

作者信息

Sabat M, Johnson C R

机构信息

Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA.

出版信息

Org Lett. 2000 Apr 20;2(8):1089-92. doi: 10.1021/ol005645i.

DOI:10.1021/ol005645i

PMID:10804561

Abstract

[formula: see text] (R and S)-alpha-Amino alcohols and alpha-amino acids, including 4-methoxyhomophenylalanine, with a variety of unnatural side chains have been synthesized via palladium-catalyzed cross-coupling Suzuki reactions. The key building blocks 1 and 2, synthesized from the common achiral precursor 2-butene-1,4-diol, were made enantiopure utilizing a Pseudomonas cepacia lipase-catalyzed kinetic resolution. The optimal conditions for the Suzuki cross-coupling and the subsequent oxidations of the resultant alpha-amino alcohols are described.

摘要

[式：见正文] （R和S）-α-氨基醇和α-氨基酸，包括具有各种非天然侧链的4-甲氧基高苯丙氨酸，已通过钯催化的交叉偶联铃木反应合成。由常见的非手性前体2-丁烯-1,4-二醇合成的关键构建块1和2，利用洋葱假单胞菌脂肪酶催化的动力学拆分使其成为对映体纯的。描述了铃木交叉偶联以及所得α-氨基醇后续氧化的最佳条件。