A rapid, simple route to homochiral alpha,beta-epoxyketones

Authors
Meth-Cohn, O Chen, Y
Citation
O. Meth-cohn et Y. Chen, A rapid, simple route to homochiral alpha,beta-epoxyketones, TETRAHEDR L, 40(33), 1999, pp. 6069-6072
Citations number
10
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
33
Year of publication
1999
Pages
6069 - 6072
Database
ISI
SICI code
0040-4039(19990813)40:33<6069:ARSRTH>2.0.ZU;2-Q
Abstract
Substituted E- or Z-acrylylamides derived from a homochiral amine such as ( R,R)-2,5-dimethylpyrrolidine or (S,S)-bis(2-phenylethyl)amine are readily e poxidised with complete stereocontrol with t-BuO2Li to give two readily sep arated, enantiomerically pure diastereomeric epoxides. The easily separated epoxides are efficiently converted into alpha,beta-epoxyketones by the act ion of organolithiums with 92->99% ee. (C) 1999 Elsevier Science Ltd. All r ights reserved.