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. 2010 Mar 3;132(8):2510-1.
doi: 10.1021/ja910187s.

Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes

Neil Grimster  1 , Li Zhang, Valery V Fokin
Affiliations

Synthesis and reactivity of rhodium(II) N-triflyl azavinyl carbenes

Neil Grimster et al. J Am Chem Soc. .

Abstract

Highly reactive rhodium(II) N-trifluoromethylsulfonyl azavinyl carbenes are formed in situ from NH-1,2,3-triazoles, triflic anhydride, and rhodium carboxylates. They rapidly and selectively react with olefins, providing cyclopropane carboxaldehydes and 2,3-dihydropyrroles in generally excellent yields and high enantio- and diastereoselectivity.

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Figures

Scheme 1
Scheme 1. Scope with respect to the olefin.a
a Reactions were performed on 0.35 mmol scale (with respect to the triazole); bthese reactions were performed in CCl4.
Scheme 2
Scheme 2. Scope with respect to the triazole.a
a Reactions were performed on 0.35 mmol scale (with respect to the triazole); bthese reactions were performed in CCl4.
See this image and copyright information in PMC

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