Asymmetric synthesis of substituted cyclopentanes via Michael initiated ring closure reactions

Tamar Yechezkel; Eugene Ghera; Namakkal G. Ramesh; Alfred Hassner

doi:10.1016/0957-4166(96)00301-1

Asymmetric synthesis of substituted cyclopentanes via Michael initiated ring closure reactions

Tamar Yechezkel, Eugene Ghera, Namakkal G. Ramesh, Alfred Hassner

Department of Chemistry

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

19 Scopus citations

Abstract

Michael initiated ring closure reactions of bromosulfone 1 and γ-oxygenated (E)-α,β-unsaturated esters, which lead stereohomogeneously to trisubstituted methylenecylopentanes, proceed also with good facial selectivity. The use of nonracemic enoate 14 in these reactions led to the synethesis of enantiomerically pure cyclopentanone 17. The reason for the preferred anti-selective Michael addition of enoate 14 with allyl and alkyl α-phenylsulfonyl lithiated reagents is discussed.

Original language	English
Pages (from-to)	2423-2436
Number of pages	14
Journal	Tetrahedron Asymmetry
Volume	7
Issue number	8
DOIs	https://doi.org/10.1016/0957-4166(96)00301-1
State	Published - Aug 1996

Bibliographical note

Funding Information:
ACKNOWLEDGEMENT. Support of this research by Grant 353/94 from the Israel Science Foundation is gratefully acknowledged. The authors thank Dr. Hugo E. Gottlieb for valuable help with the NMR spectra.

Funding

ACKNOWLEDGEMENT. Support of this research by Grant 353/94 from the Israel Science Foundation is gratefully acknowledged. The authors thank Dr. Hugo E. Gottlieb for valuable help with the NMR spectra.

Funders	Funder number
Israel Science Foundation

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title = "Asymmetric synthesis of substituted cyclopentanes via Michael initiated ring closure reactions",

abstract = "Michael initiated ring closure reactions of bromosulfone 1 and γ-oxygenated (E)-α,β-unsaturated esters, which lead stereohomogeneously to trisubstituted methylenecylopentanes, proceed also with good facial selectivity. The use of nonracemic enoate 14 in these reactions led to the synethesis of enantiomerically pure cyclopentanone 17. The reason for the preferred anti-selective Michael addition of enoate 14 with allyl and alkyl α-phenylsulfonyl lithiated reagents is discussed.",

author = "Tamar Yechezkel and Eugene Ghera and Ramesh, {Namakkal G.} and Alfred Hassner",

note = "Funding Information: ACKNOWLEDGEMENT. Support of this research by Grant 353/94 from the Israel Science Foundation is gratefully acknowledged. The authors thank Dr. Hugo E. Gottlieb for valuable help with the NMR spectra.",

year = "1996",

month = aug,

doi = "10.1016/0957-4166(96)00301-1",

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AU - Yechezkel, Tamar

AU - Ghera, Eugene

AU - Ramesh, Namakkal G.

AU - Hassner, Alfred

N1 - Funding Information: ACKNOWLEDGEMENT. Support of this research by Grant 353/94 from the Israel Science Foundation is gratefully acknowledged. The authors thank Dr. Hugo E. Gottlieb for valuable help with the NMR spectra.

PY - 1996/8

Y1 - 1996/8

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Asymmetric synthesis of substituted cyclopentanes via Michael initiated ring closure reactions

Abstract

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