Catalytic enantioselective carbon insertion into the β-vinyl C-H bond of cyclic enones

Sung Il Lee; Geum Sook Hwang; Do Hyun Ryu

doi:10.1021/ja402873b

Catalytic enantioselective carbon insertion into the β-vinyl C-H bond of cyclic enones

Sung Il Lee
, Geum Sook Hwang
, Do Hyun Ryu

Department of Chemistry

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

46 Scopus citations

Abstract

Chiral oxazaborolidinium ion-catalyzed Csp²-H functionalization of enones using diazoacetate has been developed. Various β-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.

Original language	English
Pages (from-to)	7126-7129
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	19
DOIs	https://doi.org/10.1021/ja402873b
State	Published - 15 May 2013

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title = "Catalytic enantioselective carbon insertion into the β-vinyl C-H bond of cyclic enones",

abstract = "Chiral oxazaborolidinium ion-catalyzed Csp2-H functionalization of enones using diazoacetate has been developed. Various β-substituted cyclic enones were synthesized in high yield (up to 99\%) with high to excellent enantioselectivity (up to 99\% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.",

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AU - Lee, Sung Il

AU - Hwang, Geum Sook

AU - Ryu, Do Hyun

PY - 2013/5/15

Y1 - 2013/5/15

N2 - Chiral oxazaborolidinium ion-catalyzed Csp2-H functionalization of enones using diazoacetate has been developed. Various β-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.

AB - Chiral oxazaborolidinium ion-catalyzed Csp2-H functionalization of enones using diazoacetate has been developed. Various β-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.

UR - https://www.scopus.com/pages/publications/84877811039

U2 - 10.1021/ja402873b

DO - 10.1021/ja402873b

M3 - Article

AN - SCOPUS:84877811039

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EP - 7129

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 19

ER -

Catalytic enantioselective carbon insertion into the β-vinyl C-H bond of cyclic enones

Abstract

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