Enantioselective hydrolysis of N-acylated alpha-amino esters at a biphasic interface: tandem reaction kinetic resolution using a chiral complexing agent

Seth E Snyder; William H Pirkle

doi:10.1021/ol026517s

Enantioselective hydrolysis of N-acylated alpha-amino esters at a biphasic interface: tandem reaction kinetic resolution using a chiral complexing agent

Org Lett. 2002 Sep 19;4(19):3283-6. doi: 10.1021/ol026517s.

Authors

Seth E Snyder¹, William H Pirkle

Affiliation

¹ School of Chemical Sciences, University of Illinois at Urbana-Champaign, 61801, USA. sesnyder@uiuc.edu

PMID: 12227769
DOI: 10.1021/ol026517s

Abstract

[reaction: see text] Highly enantioselective hydrolytic kinetic resolutions of esters derived from N-acylated alpha-amino acids proceed rapidly at hydrocarbon/water interfaces in the presence of a proline-derived chiral selector. When performed in tandem with an enantioselective biphasic esterification reaction, esters of 100% enantiomeric excess are obtained