使用掩蔽的氧代亚磺酰亚胺（N-亚磺酰基亚胺）不对称合成环状α-氨基膦酸酯。

Asymmetric synthesis of cyclic alpha-amino phosphonates using masked oxo sulfinimines (N-sulfinyl imines).

作者信息

Davis Franklin A, Lee Seung H, Xu He

机构信息

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

出版信息

J Org Chem. 2004 May 28;69(11):3774-81. doi: 10.1021/jo040127x.

DOI:10.1021/jo040127x

PMID:15153008

Abstract

Five-, six-, and seven-membered cyclic alpha-amino phosphonates, amino acid surrogates, are prepared in enantiomerically pure form via the highly diastereomeric addition of metal phosphonates to masked oxo sulfinimines. Hydrolysis of the resulting masked oxo alpha-amino phosphonates followed by reduction of the intermediate cyclic imino phosphonates affords the title compounds in good yield.

摘要

五元、六元和七元环状α-氨基膦酸酯（氨基酸替代物）通过金属膦酸酯与掩蔽的氧代亚磺酰亚胺的高度非对映选择性加成反应，以对映体纯的形式制备。所得掩蔽的氧代α-氨基膦酸酯水解，随后还原中间的环状亚氨基膦酸酯，以良好的产率得到标题化合物。