Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates

Ernst Urban; Gerhard Richs; Guido Knühl

doi:10.1016/0040-4020(95)00676-Y

Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates

Ernst Urban
, Gerhard Richs
, Guido Knühl

Department of Pharmaceutical Sciences

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 °C and deprotection by methanolysis gave enantiomericaJly pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.

Original language	English
Pages (from-to)	11149-11164
Number of pages	16
Journal	Tetrahedron
Volume	51
Issue number	41
DOIs	https://doi.org/10.1016/0040-4020(95)00676-Y
Publication status	Published - 9 Oct 1995

Funding

Acknowledgments: This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. E. Urban thanks Prof. G. Helmchen for the generous support of this project and the Austrian Fonds zur Forderung der wissenschaftlichen Forschung for a scholarship (J0638-CHE).

Austrian Fields of Science 2012

301207 Pharmaceutical chemistry

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10.1016/0040-4020(95)00676-Y

Cite this

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title = "Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates",

abstract = "Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 °C and deprotection by methanolysis gave enantiomericaJly pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.",

author = "Ernst Urban and Gerhard Richs and Guido Kn{\"u}hl",

note = "Funding Information: Acknowledgments: This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. E. Urban thanks Prof. G. Helmchen for the generous support of this project and the Austrian Fonds zur Forderung der wissenschaftlichen Forschung for a scholarship (J0638-CHE).",

year = "1995",

month = oct,

day = "9",

doi = "10.1016/0040-4020(95)00676-Y",

language = "English",

volume = "51",

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T1 - Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates

AU - Urban, Ernst

AU - Richs, Gerhard

AU - Knühl, Guido

N1 - Funding Information: Acknowledgments: This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. E. Urban thanks Prof. G. Helmchen for the generous support of this project and the Austrian Fonds zur Forderung der wissenschaftlichen Forschung for a scholarship (J0638-CHE).

PY - 1995/10/9

Y1 - 1995/10/9

N2 - Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 °C and deprotection by methanolysis gave enantiomericaJly pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.

AB - Asymmetric shielded 2-oxo-cyclohexenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclohexanecarboxylate 2 with camphor derived concave alcohols 1n and 1x and by subsequent introduction of a double bond via phenylselenides. Diastereoselective conjugate addition of equimolar amounts of mixed cuprates at -78 °C and deprotection by methanolysis gave enantiomericaJly pure 6-substituted 2-oxo-cyclohexanecarboxylates 14-19 and ent-14-19, valuable as chiral building blocks in natural product synthesis.

UR - https://www.scopus.com/pages/publications/0029087721

U2 - 10.1016/0040-4020(95)00676-Y

DO - 10.1016/0040-4020(95)00676-Y

M3 - Article

AN - SCOPUS:0029087721

SN - 0040-4020

VL - 51

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JO - Tetrahedron

JF - Tetrahedron

IS - 41

ER -

Enantiomerically Pure 6-Substituted 2-Oxo-cyclohexanecarboxylates by Conjugate Addition of Cuprates to Asymmetric Shielded 2-Oxo-cyclohexenecarboxylates

Abstract

Funding

Austrian Fields of Science 2012

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