Asymmetric synthesis of anti- and syn-2,3-diamino esters using sulfinimines. Water and concentration effects.

ABSTRACT: [reaction: see text] In the absence of water, an excess of the lithium enolate of N-(diphenylmethylene)glycine ethyl ester (4) adds to sulfinimines to give syn-2,3-diamino esters 6, and in the presence of water, this enolate gives the anti-2,3-diamino esters 5. These unusual results are interpreted in terms of those factors that inhibit the retro-Mannich fragmentation in the diamino esters.

SUBMITTER: Davis FA 

PROVIDER: S-EPMC2533706 | biostudies-literature | 2007 Mar

REPOSITORIES: biostudies-literature