使用(S)-(+)-2,4,6-三甲基苯基亚磺酰胺改进氮丙啶-2-膦酸酯的不对称合成。

Improved asymmetric synthesis of aziridine 2-phosphonates using (S)-(+)-2,4,6-trimethylphenylsulfinamide.

作者信息

Davis Franklin A, Ramachandar Tokala, Wu Yongzhong

机构信息

Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA.

出版信息

J Org Chem. 2003 Sep 5;68(18):6894-8. doi: 10.1021/jo030142m.

DOI:10.1021/jo030142m

PMID:12946128

Abstract

The aza-Darzens reaction of lithium diethyl iodomethylphosphonate with enantiopure N-(2,4,6-trimethylphenylsulfinyl)imines affords a single diastereomeric N-sulfinylaziridine 2-phosphonate which, on treatment with MeMgBr, gives the corresponding NH-aziridine 2-phosphonate chiral building blocks. An improved asymmetric synthesis of (S)-(+)-2,4,6-trimethylphenylsulfinamide is also given.

摘要

二乙基碘甲基膦酸锂与对映体纯的N-(2,4,6-三甲基苯基亚磺酰基)亚胺的氮杂-Darzens反应得到单一非对映异构的N-亚磺酰基氮丙啶-2-膦酸酯，用甲基溴化镁处理该产物，得到相应的NH-氮丙啶-2-膦酸酯手性砌块。还给出了(S)-(+)-2,4,6-三甲基苯基亚磺酰胺的改进的不对称合成方法。