ASYMMETRIC NITRONE-VINYL SULFOXIDE CYCLOADDITIONS

Authors
LOUIS C HOOTELE C
Citation
C. Louis et C. Hootele, ASYMMETRIC NITRONE-VINYL SULFOXIDE CYCLOADDITIONS, Tetrahedron : asymmetry, 8(1), 1997, pp. 109-131
Citations number
46
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
1
Year of publication
1997
Pages
109 - 131
Database
ISI
SICI code
0957-4166(1997)8:1<109:ANSC>2.0.ZU;2-J
Abstract
The cycloaddition of (Z) and (E)-vinyl sulfoxides with cyclic nitrones 1 and 2 is reported. Best diastereoselection is achieved with (Z)-vin yl sulfoxides 7a-d as dipolarophiles. This methodology allows the high ly stereoselective synthesis of (+)-sedridine 9a, (-)-hygroline 10 and (-)-(2S)-N-carbomethoxypelletierine 11a. (C) 1997, Elsevier Science L td. All rights reserved.