Transition metal-catalyzed hydro-, sila-, and stannastannation of cyclopropenes: Stereo- and regioselective approach toward multisubstituted cyclopropyl synthons

Marina Rubina, Michael Rubin, Vladimir Gevorgyan

Research output: Contribution to journalArticle

72 Citations (Scopus)

Abstract

The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

Original languageEnglish (US)
Pages (from-to)11566-11567
Number of pages2
JournalJournal of the American Chemical Society
Volume124
Issue number39
DOIs
StatePublished - Oct 2 2002
Externally publishedYes

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Palladium
Transition metals
Metals
Economics
Atoms
cyclopropene

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

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abstract = "The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.",
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T1 - Transition metal-catalyzed hydro-, sila-, and stannastannation of cyclopropenes

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AU - Rubina, Marina

AU - Rubin, Michael

AU - Gevorgyan, Vladimir

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AB - The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.

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