Catalytic enantioselective hydroboration of cyclopropenes

Marina Rubina, Michael Rubin, Vladimir Gevorgyan

Research output: Contribution to journalArticle

203 Citations (Scopus)

Abstract

2,2-Disubstituted cyclopropyl boronates have been synthesized with high degrees of diastereo- and enantioselectivity via the rhodium-catalyzed asymmetric hydroboration of 3,3-disubstituted cyclopropenes. A strong directing effect of ester and alkoxymethyl substituents has been demonstrated. The directing effect was found to be necessary in achieving high degrees of enantiomeric induction. Selected cyclopropylboronic derivatives were successfully employed in the Suzuki cross-coupling reaction to produce the corresponding optically active aryl- and vinylcyclopropanes in good yields.

Original languageEnglish (US)
Pages (from-to)7198-7199
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number24
DOIs
StatePublished - Jun 18 2003
Externally publishedYes

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Rhodium
Enantioselectivity
Cross Reactions
Esters
Derivatives

ASJC Scopus subject areas

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

Cite this

Catalytic enantioselective hydroboration of cyclopropenes. / Rubina, Marina; Rubin, Michael; Gevorgyan, Vladimir.

In: Journal of the American Chemical Society, Vol. 125, No. 24, 18.06.2003, p. 7198-7199.

Research output: Contribution to journalArticle

Rubina, Marina ; Rubin, Michael ; Gevorgyan, Vladimir. / Catalytic enantioselective hydroboration of cyclopropenes. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 24. pp. 7198-7199.
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