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

Ritobroto Sengupta; Jason A. Witek; Steven M. Weinreb

doi:10.1016/j.tet.2011.08.054

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

Ritobroto Sengupta, Jason A. Witek, Steven M. Weinreb

Chemistry

Research output: Contribution to journal › Article › peer-review

16 Scopus citations

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.

Original language	English (US)
Pages (from-to)	8229-8234
Number of pages	6
Journal	Tetrahedron
Volume	67
Issue number	43
DOIs	https://doi.org/10.1016/j.tet.2011.08.054
State	Published - Oct 28 2011

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.08.054

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title = "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.",

author = "Ritobroto Sengupta and Witek, {Jason A.} and Weinreb, {Steven M.}",

note = "Funding Information: We are grateful to the National Institutes of Health ( GM-087733 ) and the National Science Foundation ( CHE-0806807 ) for financial support of this research. We also thank Dr. H. Yennawar (Penn State Small Molecule X-Ray Cystallographic Facility) for the X-ray crystal structure determinations. ",

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T1 - Stereochemical investigation of conjugate additions of carbon- and heteronucleophiles to ring-substituted nitrosocyclohexenes

AU - Sengupta, Ritobroto

AU - Witek, Jason A.

AU - Weinreb, Steven M.

N1 - Funding Information: We are grateful to the National Institutes of Health ( GM-087733 ) and the National Science Foundation ( CHE-0806807 ) for financial support of this research. We also thank Dr. H. Yennawar (Penn State Small Molecule X-Ray Cystallographic Facility) for the X-ray crystal structure determinations.

PY - 2011/10/28

Y1 - 2011/10/28

N2 - 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.

AB - 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.

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U2 - 10.1016/j.tet.2011.08.054

DO - 10.1016/j.tet.2011.08.054

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JO - Tetrahedron

JF - Tetrahedron

IS - 43

ER -

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

Abstract

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