Enyne cross-metathesis with strained, geminally-substituted alkenes: Direct access to highly substituted 1,3-dienes

Daniel A. Clark; Brenda S. Basile; William S. Karnofel; Steven T. Diver

doi:10.1021/ol802007q

Enyne cross-metathesis with strained, geminally-substituted alkenes: Direct access to highly substituted 1,3-dienes

Daniel A. Clark, Brenda S. Basile, William S. Karnofel, Steven T. Diver

Department of Chemistry

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

25 Scopus citations

Abstract

(Figure Presented) Ru cat. = variety of second generation Grubbs' catalysts used nine examples, 92-99% isolated yields Angle strain in methylene cyclobutane was used to drive a cross-enyne metathesis with 1-alkynes, giving 1,1,3-trisubstituted 1,3-dienes in good isolated yields. An extensive survey of Grubbs' second-generation catalysts led to an optimized reaction conducted at 0 °C.

Original language	English (US)
Pages (from-to)	4927-4929
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	21
DOIs	https://doi.org/10.1021/ol802007q
State	Published - 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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abstract = "(Figure Presented) Ru cat. = variety of second generation Grubbs' catalysts used nine examples, 92-99% isolated yields Angle strain in methylene cyclobutane was used to drive a cross-enyne metathesis with 1-alkynes, giving 1,1,3-trisubstituted 1,3-dienes in good isolated yields. An extensive survey of Grubbs' second-generation catalysts led to an optimized reaction conducted at 0 °C.",

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T1 - Enyne cross-metathesis with strained, geminally-substituted alkenes

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AU - Basile, Brenda S.

AU - Karnofel, William S.

AU - Diver, Steven T.

PY - 2008

Y1 - 2008

N2 - (Figure Presented) Ru cat. = variety of second generation Grubbs' catalysts used nine examples, 92-99% isolated yields Angle strain in methylene cyclobutane was used to drive a cross-enyne metathesis with 1-alkynes, giving 1,1,3-trisubstituted 1,3-dienes in good isolated yields. An extensive survey of Grubbs' second-generation catalysts led to an optimized reaction conducted at 0 °C.

AB - (Figure Presented) Ru cat. = variety of second generation Grubbs' catalysts used nine examples, 92-99% isolated yields Angle strain in methylene cyclobutane was used to drive a cross-enyne metathesis with 1-alkynes, giving 1,1,3-trisubstituted 1,3-dienes in good isolated yields. An extensive survey of Grubbs' second-generation catalysts led to an optimized reaction conducted at 0 °C.

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Enyne cross-metathesis with strained, geminally-substituted alkenes: Direct access to highly substituted 1,3-dienes

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