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

Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes
Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes
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.
tandem radical cyclization, transfer chain-reaction, aliphatic nitro-groups, electron-transfer, hydrogen, replacement, hydride, 1-benzyl-1, 4-dihydronicotinamide, denitration, reagent
0957-4166
1673-1675
Gil, M.V.
3ba9dd82-e26f-43e2-a7ee-b8ce3361219a
Román, E.
9d18a1e4-53de-4a32-bee9-4451d1ae5995
Serrano, J.A.
777244b5-9b7b-423b-8520-eafd68064638
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161
Gil, M.V.
3ba9dd82-e26f-43e2-a7ee-b8ce3361219a
Román, E.
9d18a1e4-53de-4a32-bee9-4451d1ae5995
Serrano, J.A.
777244b5-9b7b-423b-8520-eafd68064638
Hursthouse, M.B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Light, M.E.
cf57314e-6856-491b-a8d2-2dffc452e161

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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More information

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

Identifiers

Local EPrints ID: 19496
URI: http://eprints.soton.ac.uk/id/eprint/19496
ISSN: 0957-4166
PURE UUID: 7df705e7-dbd0-4e7e-a966-c5b1003a9043
ORCID for M.E. Light: ORCID iD orcid.org/0000-0002-0585-0843

Catalogue record

Date deposited: 16 Feb 2006
Last modified: 19 Nov 2019 01:53

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