Asymmetric synthesis of anti- and syn-2,3-diamino esters using sulfinimines. Water and concentration effects.
[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.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Zhang
Yanfeng
Y
Qiu
Hui
H
D000586:Amination; D004952:Esters / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
D004952:Esters; D007097:Imines; D014867:Water; D013455:Sulfur