Palladium(0) catalyzed enantioselective rearrangement of O-allylic thiocarbamates to S-allylic thiocarbamates: asymmetric synthesis of allylic thiols

Authors
Bohme, A Gais, HJ
Citation
A. Bohme et Hj. Gais, Palladium(0) catalyzed enantioselective rearrangement of O-allylic thiocarbamates to S-allylic thiocarbamates: asymmetric synthesis of allylic thiols, TETRAHEDR-A, 10(13), 1999, pp. 2511-2514
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
13
Year of publication
1999
Pages
2511 - 2514
Database
ISI
SICI code
0957-4166(19990702)10:13<2511:PCEROO>2.0.ZU;2-9
Abstract
The Pd(0) catalyzed rearrangement of the O-allylic thiocarbamates rac-2a, r ac-2b and rac-4 in the presence of the chiral bisphosphane 5 proceeded quan titatively and gave the S-allylic thiocarbamates 6a, 6b and 7, respectively , with 91, 92 and 97% ee, respectively, in high yields. Saponification of t he S-allylic thiocarbamate 7 furnished the allylic thiol 9 with 97% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.