An "anti-Baldwin" 3-Exo-dig cyclization: Preparation of vinylidene cyclopropanes from electron-poor alkenes

Matthew J. Campbell; Patrick D. Pohlhaus; Geanna Min; Kohsuke Ohmatsu; Jeffrey S. Johnson

doi:10.1021/ja803553a

An "anti-Baldwin" 3-Exo-dig cyclization: Preparation of vinylidene cyclopropanes from electron-poor alkenes

Matthew J. Campbell
, Patrick D. Pohlhaus
, Geanna Min
, Kohsuke Ohmatsu
, Jeffrey S. Johnson

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

44 Citations (Scopus)

Abstract

Stabilized carbanions undergo an uncommon 3-exodig cyclization onto propargyl halides through an S_N2′ substitution. Propargyl iodides as electrophiles are necessary to achieve good yields (36-95%) for most substrates, although the usefulness of chlorides and bromides is documented. A variety of monocyclic and bicyclic vinylidene cyclopropanes can be prepared. These products are not available by standard carbene methodology.

Original language	English
Pages (from-to)	9180-9181
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	29
DOIs	https://doi.org/10.1021/ja803553a
Publication status	Published - 2008 Jul 23
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja803553a

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AU - Johnson, Jeffrey S.

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An "anti-Baldwin" 3-Exo-dig cyclization: Preparation of vinylidene cyclopropanes from electron-poor alkenes

Abstract

ASJC Scopus subject areas

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