Catalytic and asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement

Authors
Fukuda, T Irie, R Katsuki, T
Citation
T. Fukuda et al., Catalytic and asymmetric [2,3]sigmatropic rearrangement: Co(III)-salen catalyzed S-ylide formation from allyl aryl sulfides and their rearrangement, TETRAHEDRON, 55(3), 1999, pp. 649-664
Citations number
30
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
3
Year of publication
1999
Pages
649 - 664
Database
ISI
SICI code
0040-4020(19990115)55:3<649:CAA[RC>2.0.ZU;2-H
Abstract
Reaction of allyl aryl sulfides and a-diazoacetic acid esters in the presen ce of optically active Co(III)-salen complex (8-Br) provided 3-substituted 2-arylthio-4-pentenoic acid esters stereoselectively py way of enantioselec tive S-ylide formation and subsequent diastereoselective [2,3]sigmatropic r earrangement. For example, the reaction of cinnamyl phenyl sulfide and (-)- menthyl alpha-diazoacetate provided (-)-menthyl (2R,3S)-2-phenylthio-3-phen yl-4-pentenoate of 74% de preferentially. (C) 1998 Elsevier Science Ltd. Al l rights reserved.