A novel asymmetric synthesis of 2-azetidinones from achiral precursors

Authors
Zhou, F Detty, MR Lachicotte, RJ
Citation
F. Zhou et al., A novel asymmetric synthesis of 2-azetidinones from achiral precursors, TETRAHEDR L, 40(4), 1999, pp. 585-588
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
4
Year of publication
1999
Pages
585 - 588
Database
ISI
SICI code
0040-4039(19990122)40:4<585:ANASO2>2.0.ZU;2-#
Abstract
Asymmetric synthesis of (3S,4S)-3-phenylsulfonyl-4-phenylazetidin-2-ones in up to 46% ee from achiral amines and 2-phenylsulfonyl-3-phenylpropenoyl ch loride was achieved with chiral Lewis-acid catalysis by salen-copper(II) co mplexes derived from (1R, 2R)-(-)-1,2-diaminocyclohexane. The absolute conf iguration was assigned by single crystal, X-ray crystallographic analyis of enantiomerically pure (3S,4S)-(-)-3-phenylsulfonyl-4-phenylazetidin-2-one (7). (C) 1999 Elsevier Science Ltd. All rights reserved.