EPC synthesis of 6-substituted 2-oxo-cyclohexanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclohexenecarboxylates

Ernst Urban; Gerhard Riehs; Guido Knühl

doi:10.1016/00404-0399(50)0886H-

EPC synthesis of 6-substituted 2-oxo-cyclohexanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclohexenecarboxylates

Ernst Urban
, Gerhard Riehs
, 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 enantiomerically 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)	4773-4776
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	27
DOIs	https://doi.org/10.1016/00404-0399(50)0886H-
Publication status	Published - 3 Jul 1995

Austrian Fields of Science 2012

301207 Pharmaceutical chemistry

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title = "EPC synthesis of 6-substituted 2-oxo-cyclohexanecarboxylates via 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 enantiomerically 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 Riehs and Guido Kn{\"u}hl",

year = "1995",

month = jul,

day = "3",

doi = "10.1016/00404-0399(50)0886H-",

language = "English",

volume = "36",

pages = "4773--4776",

journal = "Tetrahedron Letters",

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T1 - EPC synthesis of 6-substituted 2-oxo-cyclohexanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclohexenecarboxylates

AU - Urban, Ernst

AU - Riehs, Gerhard

AU - Knühl, Guido

PY - 1995/7/3

Y1 - 1995/7/3

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 enantiomerically 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 enantiomerically 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/85047673523

U2 - 10.1016/00404-0399(50)0886H-

DO - 10.1016/00404-0399(50)0886H-

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SN - 0040-4039

VL - 36

SP - 4773

EP - 4776

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 27

ER -

EPC synthesis of 6-substituted 2-oxo-cyclohexanecarboxylates via conjugate addition of cuprates to asymmetric shielded 2-oxo-cyclohexenecarboxylates

Abstract

Austrian Fields of Science 2012

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