Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes

Stepan Chuprakov, Brady T. Worrell, Nicklas Selander, Rakesh K. Sit, Valery V. Fokin

Research output: Contribution to journalArticle

149 Citations (Scopus)

Abstract

Rhodium(II) azavinyl carbenes, conveniently generated from 1-sulfonyl-1,2,3-triazoles, undergo a facile, mild, and convergent formal 1,3-insertion into N-H and O-H bonds of primary and secondary amides, various alcohols, and carboxylic acids to afford a wide range of vicinally bisfunctionalized (Z)-olefins with perfect regio- and stereoselectivity. Utilizing the distinctive functionality installed through these reactions, a number of subsequent rearrangements and cyclizations expand the repertoire of valuable organic building blocks constructed by reactions of transition-metal carbene complexes, including α-allenyl ketones and amino-substituted heterocycles.

Original languageEnglish
Pages (from-to)195-202
Number of pages8
JournalJournal of the American Chemical Society
Volume136
Issue number1
DOIs
Publication statusPublished - 8 Jan 2014
Externally publishedYes

ASJC Scopus subject areas

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

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  • Cite this

    Chuprakov, S., Worrell, B. T., Selander, N., Sit, R. K., & Fokin, V. V. (2014). Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes. Journal of the American Chemical Society, 136(1), 195-202. https://doi.org/10.1021/ja408185c