EPC synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates

Ernst Urban; Guido Knühl; Günter Helmchen

doi:10.1016/0040-4039(95)01537-R

EPC synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates

Ernst Urban
, Guido Knühl
, Günter Helmchen

Department of Pharmaceutical Sciences

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Asymmetric shielded 2-oxo-cyclopentenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclopentanecarboxylate 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 ethanolysis gave enantiomerically pure 5-substituted 2-oxo-cyclopentanecarboxylates 13-18 and ent-13-18, valuable as chiral building blocks in natural product synthesis.

Original language	English
Pages (from-to)	7229-7232
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	40
DOIs	https://doi.org/10.1016/0040-4039(95)01537-R
Publication status	Published - 2 Oct 1995

Funding

Acknowledgments: This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. E. Urban thanks the Austrian Fonds zur F6rderung der wissenschaftlichen Forschung for a scholarship (J0638-CHE).

Austrian Fields of Science 2012

301207 Pharmaceutical chemistry

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10.1016/0040-4039(95)01537-R

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title = "EPC synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates",

abstract = "Asymmetric shielded 2-oxo-cyclopentenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclopentanecarboxylate 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 ethanolysis gave enantiomerically pure 5-substituted 2-oxo-cyclopentanecarboxylates 13-18 and ent-13-18, valuable as chiral building blocks in natural product synthesis.",

author = "Ernst Urban and Guido Kn{\"u}hl and G{\"u}nter Helmchen",

note = "Funding Information: Acknowledgments: This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. E. Urban thanks the Austrian Fonds zur F6rderung der wissenschaftlichen Forschung for a scholarship (J0638-CHE).",

year = "1995",

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doi = "10.1016/0040-4039(95)01537-R",

language = "English",

volume = "36",

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journal = "Tetrahedron Letters",

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T1 - EPC synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates

AU - Urban, Ernst

AU - Knühl, Guido

AU - Helmchen, Günter

N1 - Funding Information: Acknowledgments: This work was supported by the Deutsche Forschungsgemeinschaft and the Fonds der Chemischen Industrie. E. Urban thanks the Austrian Fonds zur F6rderung der wissenschaftlichen Forschung for a scholarship (J0638-CHE).

PY - 1995/10/2

Y1 - 1995/10/2

N2 - Asymmetric shielded 2-oxo-cyclopentenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclopentanecarboxylate 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 ethanolysis gave enantiomerically pure 5-substituted 2-oxo-cyclopentanecarboxylates 13-18 and ent-13-18, valuable as chiral building blocks in natural product synthesis.

AB - Asymmetric shielded 2-oxo-cyclopentenecarboxylates 6n and 6x were prepared by transesterification of 2-oxo-cyclopentanecarboxylate 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 ethanolysis gave enantiomerically pure 5-substituted 2-oxo-cyclopentanecarboxylates 13-18 and ent-13-18, valuable as chiral building blocks in natural product synthesis.

UR - https://www.scopus.com/pages/publications/0029164289

U2 - 10.1016/0040-4039(95)01537-R

DO - 10.1016/0040-4039(95)01537-R

M3 - Article

AN - SCOPUS:0029164289

SN - 0040-4039

VL - 36

SP - 7229

EP - 7232

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

EPC synthesis of 5-substituted 2-oxo-cyclopentanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclopentenecarboxylates

Abstract

Funding

Austrian Fields of Science 2012

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