Novel intramolecular cyclopropanation reaction of unsaturated β-keto esters

Dan Yang; Qiang Gao; Chi Sing Lee; Kung Kai Cheung

doi:10.1021/ol0265158

Novel intramolecular cyclopropanation reaction of unsaturated β-keto esters

Dan Yang^*
, Qiang Gao
, Chi Sing Lee
, Kung Kai Cheung

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Journal article › peer-review

50 Citations (Scopus)

Abstract

Fused cyclopropane β-keto esters are versatile intermediates for the synthesis of many biologically active natural products. Here we report a new intramolecular cyclopropanation reaction of unsaturated β-keto esters. In the presence of l₂, Et₃N, and Lewis acids such as Mg(CIO₄)₂ and Yb(OTf)₃, β-keto esters 1 bearing various olefin substituents were transformed to fused cyclopropanes 2 in a highly stereospecific manner with moderate to good yields. The mechanism of the reaction was also investigated.

Original language	English
Pages (from-to)	3271-3274
Number of pages	4
Journal	Organic Letters
Volume	4
Issue number	19
DOIs	https://doi.org/10.1021/ol0265158
Publication status	Published - 1 Sept 2002

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10.1021/ol0265158

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title = "Novel intramolecular cyclopropanation reaction of unsaturated β-keto esters",

abstract = "Fused cyclopropane β-keto esters are versatile intermediates for the synthesis of many biologically active natural products. Here we report a new intramolecular cyclopropanation reaction of unsaturated β-keto esters. In the presence of l2, Et3N, and Lewis acids such as Mg(CIO4)2 and Yb(OTf)3, β-keto esters 1 bearing various olefin substituents were transformed to fused cyclopropanes 2 in a highly stereospecific manner with moderate to good yields. The mechanism of the reaction was also investigated.",

author = "Dan Yang and Qiang Gao and Lee, \{Chi Sing\} and Cheung, \{Kung Kai\}",

note = "Publisher Copyright: {\textcopyright} 2002 American Chemical Society. Funding Information: This work was supported by The University of Hong Kong and Hong Kong Research Grants Council. D.Y. acknowledges the Bristol-Myers Squibb Foundation for an Unrestricted Grant in Synthetic Organic Chemistry and the Croucher Foundation for a Croucher Senior Research Fellowship Award.",

year = "2002",

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doi = "10.1021/ol0265158",

language = "English",

volume = "4",

pages = "3271--3274",

journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Novel intramolecular cyclopropanation reaction of unsaturated β-keto esters

AU - Yang, Dan

AU - Gao, Qiang

AU - Lee, Chi Sing

AU - Cheung, Kung Kai

N1 - Publisher Copyright: © 2002 American Chemical Society. Funding Information: This work was supported by The University of Hong Kong and Hong Kong Research Grants Council. D.Y. acknowledges the Bristol-Myers Squibb Foundation for an Unrestricted Grant in Synthetic Organic Chemistry and the Croucher Foundation for a Croucher Senior Research Fellowship Award.

PY - 2002/9/1

Y1 - 2002/9/1

N2 - Fused cyclopropane β-keto esters are versatile intermediates for the synthesis of many biologically active natural products. Here we report a new intramolecular cyclopropanation reaction of unsaturated β-keto esters. In the presence of l2, Et3N, and Lewis acids such as Mg(CIO4)2 and Yb(OTf)3, β-keto esters 1 bearing various olefin substituents were transformed to fused cyclopropanes 2 in a highly stereospecific manner with moderate to good yields. The mechanism of the reaction was also investigated.

AB - Fused cyclopropane β-keto esters are versatile intermediates for the synthesis of many biologically active natural products. Here we report a new intramolecular cyclopropanation reaction of unsaturated β-keto esters. In the presence of l2, Et3N, and Lewis acids such as Mg(CIO4)2 and Yb(OTf)3, β-keto esters 1 bearing various olefin substituents were transformed to fused cyclopropanes 2 in a highly stereospecific manner with moderate to good yields. The mechanism of the reaction was also investigated.

UR - https://www.scopus.com/pages/publications/0041758456

U2 - 10.1021/ol0265158

DO - 10.1021/ol0265158

M3 - Journal article

AN - SCOPUS:0041758456

SN - 1523-7060

VL - 4

SP - 3271

EP - 3274

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Novel intramolecular cyclopropanation reaction of unsaturated β-keto esters

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