ASYMMETRIC INDUCTION IN YLIDENE-5-O-VINYL-D-GLYCOFURANOSES(2]CYCLOADDITION OF CHLOROSULFONYL ISOCYANATE TO 1,2)

Authors
KALUZA Z FURMAN B CHMIELEWSKI M
Citation
Z. Kaluza et al., ASYMMETRIC INDUCTION IN YLIDENE-5-O-VINYL-D-GLYCOFURANOSES(2]CYCLOADDITION OF CHLOROSULFONYL ISOCYANATE TO 1,2), Tetrahedron : asymmetry, 6(7), 1995, pp. 1719-1730
Citations number
4
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
7
Year of publication
1995
Pages
1719 - 1730
Database
ISI
SICI code
0957-4166(1995)6:7<1719:AIIY>2.0.ZU;2-7
Abstract
The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2- O-isopropylidene-5-O-vinyl-D-glycofuranoses is presented. The stereose lectivity strongly depends on substitution and configuration at the C- 3 carbon atom. A small substituent at C-3 or allo configuration of the sugar promote excellent stereoselectivity, affording (s) configuratio n at the C-4' carbon atom of the azetidinone ring. Intramolecular cycl ization in compounds 20, 22-26, and 31 provides the respective clavams 32-38.