胍叶立德向3-烯基（或3-炔基）氮杂环丙烷-2-羧酸酯的手性转移及其在(2R,3S)-3-羟基亮氨酸和D-赤藓糖神经鞘氨醇合成中的应用。

Chirality transfer from guanidinium ylides to 3-alkenyl (or 3-alkynyl) aziridine-2-carboxylates and application to the syntheses of (2R,3S)-3-hydroxyleucinate and D-erythro-sphingosine.

作者信息

Disadee Wannaporn, Ishikawa Tsutomu

机构信息

Graduate School of Pharmaceutical Sciences, Chiba University, Inage, Chiba 263-8522, Japan.

出版信息

J Org Chem. 2005 Nov 11;70(23):9399-406. doi: 10.1021/jo051495j.

DOI:10.1021/jo051495j

PMID:16268613

Abstract

[Reaction: see text]. Reaction of chiral guanidinium ylides with alpha,beta-unsaturated aldehydes gives 3-(alpha,beta-unsaturated) aziridine-2-carboxylates in high diastereo- and enantioselectivities (up to 93% diastereomeric excess and 98% enantiomeric excess). 3-(1-methylvinyl)- and 3-[(E)-pentadec-1-enyl]aziridine-2-carboxylates were successfully employed to prepare (2R,3S)-3-hydroxyleucinate and d-erythro-sphingosine, respectively.

摘要

[反应：见正文]。手性胍叶立德与α,β-不饱和醛反应，以高非对映选择性和对映选择性（高达93%的非对映体过量和98%的对映体过量）生成3-(α,β-不饱和)氮杂环丙烷-2-羧酸酯。3-(1-甲基乙烯基)-和3-[(E)-十五碳-1-烯基]氮杂环丙烷-2-羧酸酯分别成功用于制备(2R,3S)-3-羟基亮氨酸酯和d-赤藓糖神经鞘氨醇。