A chiral, oxidatively cleavable auxiliary in conjugate additions of lithium amides. Preparation of enantiomerically pure beta-amino acid derivatives

Authors
Podlech, J
Citation
J. Podlech, A chiral, oxidatively cleavable auxiliary in conjugate additions of lithium amides. Preparation of enantiomerically pure beta-amino acid derivatives, SYN COMMUN, 30(10), 2000, pp. 1779-1786
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
10
Year of publication
2000
Pages
1779 - 1786
Database
ISI
SICI code
0039-7911(2000)30:10<1779:ACOCAI>2.0.ZU;2-#
Abstract
Addition of enantiomerically pure 4-methoxyphenethyl-substituted lithium am ides to alpha,beta-unsaturated esters leads to beta-amino acid derivatives 4 - 7 with selectivities > 95 :5. The auxiliary can be cleaved by oxidation with cerium(IV) ammonium nitrate (CAN) and subsequent hydrolysis of the re sulting mixture of imines.