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Stereochemical investigation of conjugate additions of carbon- and heteronucleophiles to ring-substituted nitrosocyclohexenes.

ABSTRACT: Intermolecular Michael-type conjugate additions of some in situ-generated ring-substituted nitrosocyclohexenes with both carbon- and heteronucleophiles have been found to be highly stereoselective, leading predominantly (or exclusively) to products resulting from axial attack on a half-chair conformation of the nitrosoalkene substrate.

SUBMITTER: Sengupta R

PROVIDER: S-EPMC3224044 | biostudies-literature | 2011 Oct

REPOSITORIES: biostudies-literature

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Stereochemical investigation of conjugate additions of carbon- and heteronucleophiles to ring-substituted nitrosocyclohexenes.

Sengupta Ritobroto R Witek Jason A JA Weinreb Steven M SM

Tetrahedron 20111001 43

Intermolecular Michael-type conjugate additions of some in situ-generated ring-substituted nitrosocyclohexenes with both carbon- and heteronucleophiles have been found to be highly stereoselective, leading predominantly (or exclusively) to products resulting from axial attack on a half-chair conformation of the nitrosoalkene substrate. ...[more]

PMID: 22125343

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