Asymmetric syn-dihydroxylation of gamma-substituted (2R)-N-(beta,gamma-enoyl)bornane-10,2-sultams

Authors
Raczko, J Achmatowicz, M Kwiatkowski, P Chapuis, C Urbanczyk-Lipkowska, Z Jurczak, J
Citation
J. Raczko et al., Asymmetric syn-dihydroxylation of gamma-substituted (2R)-N-(beta,gamma-enoyl)bornane-10,2-sultams, TETRAHEDR-A, 11(4), 2000, pp. 1027-1041
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
11
Issue
4
Year of publication
2000
Pages
1027 - 1041
Database
ISI
SICI code
0957-4166(20000310)11:4<1027:ASOG(>2.0.ZU;2-8
Abstract
Various gamma-substituted (2R)-N-( beta,gamma-enoyl)bornane-10,2-sultams ha ve been examined in diastereoselective OsO4 syn-dihydroxylation. In contras t to the C(alpha)-atom, the bornane-10,2-sultam auxiliary exerts a very poo r influence on the C(beta)-carbon. Spontaneous stereoselective hydrolysis o f the minor diastereoisomer (3S,4S)-5c opens the way to enantiomerically pu re building blocks, (C) 2000 Elsevier Science Ltd. All rights reserved.