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

Gil, M.V., Román, E., Serrano, J.A., Hursthouse, M.B. and Light, M.E. (2001) Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes. Tetrahedron: Asymmetry, 12 (12), 1673-1675. (doi:10.1016/S0957-4166(01)00304-4).

Record type: Article

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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Published date: 16 July 2001

Keywords: tandem radical cyclization, transfer chain-reaction, aliphatic nitro-groups, electron-transfer, hydrogen, replacement, hydride, 1-benzyl-1, 4-dihydronicotinamide, denitration, reagent

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