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Synfacts 2010(2): 0197-0197  
DOI: 10.1055/s-0029-1219099
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Cyclopropanation with gem-Dizinc Reagents

Contributor(s): Hisashi Yamamoto, Zhi Li
L. E. Zimmer, A. B. Charette*
Université de Montréal, Canada
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Publikationsverlauf

Publikationsdatum:
21. Januar 2010 (online)

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Significance

Previously, the authors reported the diastereoselective cyclopropanation of allylic alcohols with gem-dizinc carbenoids (J. Am. Chem. Soc. 2005, 127, 13140). In this paper, they managed to obtain highly enantioenriched 1,2,3-tri-substituted cyclopropanes. In the aid of a dizinc reagent and a chiral dioxaborolane reagent the cyclopropyl borinate intermediate is generated and could be used in the following cross-couplings.