Highly enantio- and diastereoselective mannich reactions of chiral Ni(II) glycinates with amino sulfones. Efficient asymmetric synthesis of aromatic alpha,beta-diamino acids

Jiang Wang; Ting Shi; Guanghui Deng; Hualiang Jiang; Hong Liu

doi:10.1021/jo8019169

Highly enantio- and diastereoselective mannich reactions of chiral Ni(II) glycinates with amino sulfones. Efficient asymmetric synthesis of aromatic alpha,beta-diamino acids

J Org Chem. 2008 Nov 7;73(21):8563-70. doi: 10.1021/jo8019169. Epub 2008 Oct 10.

Authors

Jiang Wang¹, Ting Shi, Guanghui Deng, Hualiang Jiang, Hong Liu

Affiliation

¹ Drug Discovery and Design Centre, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Graduate School, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, China.

PMID: 18844412
DOI: 10.1021/jo8019169

Abstract

This paper describes a practical, enantio- and diastereoselective Mannich reaction between a chiral Ni(II) complex of glycine 1 and alpha-amino sulfones 2, involving the creation of a carbon-carbon bond and two stereogenic centers in a single operation; it represents an attractive route to the synthesis alpha,beta-diamino acids.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids, Aromatic / chemical synthesis*
Glycine / chemistry*
Nickel
Stereoisomerism
Sulfones / chemistry*

Substances

Amino Acids, Aromatic
Sulfones
Nickel
Glycine