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Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes

Authors
Journal
Tetrahedron Asymmetry
0957-4166
Publisher
Elsevier
Publication Date
Volume
12
Issue
12
Identifiers
DOI: 10.1016/s0957-4166(01)00304-4

Abstract

Abstract The denitrohydrogenation of chiral 4-alkyl-5-glyco-4-nitrocyclohex-1-enes ( 1 and 3) with tri- n-butyltin hydride and azobisisobutironitrile proceeded in a completely stereoselective way. In each case, the hydrogen atom provided by tri- n-butyltin hydride adds to a free radical intermediate in a trans mode to the adjacent, sterically demanding, sugar side-chain. Attempts to perform denitroalkylation reactions of 1a, 3a or 8 with electron-deficient alkenes yielded only denitrohydrogenated products.

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