N-烷基-(邻甲苯基)氮杂环丙烷的锂化反应：异chroman 的立体选择性合成。

Lithiation of N-alkyl-(o-tolyl)aziridine: stereoselective synthesis of isochromans.

机构信息

Dipartimento Farmaco-Chimico, Università di Bari, Consorzio Interuniversitario Nazionale Metodologie e Processi Innovativi di Sintesi C.I.N.M.P.I.S., Via E. Orabona 4, I-70125-Bari, Italy.

出版信息

J Org Chem. 2009 Aug 21;74(16):6319-22. doi: 10.1021/jo9011943.

DOI:10.1021/jo9011943

PMID:19610596

Abstract

The lithiation reaction of o-tolylaziridine 1 has been investigated by using the aziridine ring capability to act as a directing metalation group. Trapped with electrophiles, the resulting o-aziridinyl benzyllithium 1-Li gives access to several functionalized aziridines 2a-j. The hydroxyalkylated derivatives 2d-j were converted into important scaffolds such as isochromans 3a-d. A stereoselective preparation of isochromans (R)-3b, (1R,3S)-3d, and (1R,3R)-3d has been developed starting from enantioenriched o-tolylaziridine.

摘要

我们研究了邻甲苯基氮丙啶 1 的锂化反应，利用氮丙啶环的能力作为导向金属化基团。与亲电试剂捕获后，得到的邻氮丙啶基苄基锂 1-Li 可以得到几种官能化的氮丙啶 2a-j。羟基烷基化衍生物 2d-j 可以转化为重要的骨架，如异色满 3a-d。从手性富集的邻甲苯基氮丙啶出发，开发了立体选择性制备异色满 (R)-3b、(1R,3S)-3d 和 (1R,3R)-3d 的方法。