路易斯酸介导的醇对2-芳基-N-对甲苯磺酰氮杂环丁烷和氮杂环丙烷的高度区域选择性SN2型开环反应。

Lewis acid-mediated highly regioselective SN2-Type ring-opening of 2-aryl-N-tosylazetidines and aziridines by alcohols.

作者信息

Ghorai Manas K, Das Kalpataru, Shukla Dipti

机构信息

Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.

出版信息

J Org Chem. 2007 Jul 20;72(15):5859-62. doi: 10.1021/jo0703294. Epub 2007 Jun 26.

DOI:10.1021/jo0703294

PMID:17592875

Abstract

Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols to afford various 1,3-amino ethers in excellent yields with good enantiomeric excess is described. Similar SN2-type ring-opening of chiral 2-phenyl-N-tosylaziridine with various alcohols produces the corresponding nonracemic 1,2-amino ethers in excellent yields and good ee. The mechanism of the ring-opening of aziridines and azetidines via an SN2 pathway is supported by the formation of nonracemic amino ethers.

摘要

本文描述了在路易斯酸介导下，2-芳基-N-对甲苯磺酰氮杂环丁烷与醇发生高度区域选择性的SN2型开环反应，以优异的产率和良好的对映体过量得到各种1,3-氨基醚。手性2-苯基-N-对甲苯磺酰氮杂环丙烷与各种醇发生类似的SN2型开环反应，以优异的产率和良好的对映体过量得到相应的非外消旋1,2-氨基醚。非外消旋氨基醚的形成支持了氮杂环丙烷和氮杂环丁烷通过SN2途径开环的机理。