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Synfacts 2007(9): 0949-0949  
DOI: 10.1055/s-2007-968857
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Trifluoromethyl-Substituted Cyclopropanes

Contributor(s): Mark Lautens, Frédéric Ménard
J. R. Denton, D. Sukumaran, H. M. L. Davies*
The State University of New York at Buffalo, USA
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Publikationsdatum:
23. August 2007 (online)

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Significance

Methods for selective introduction of fluoroalkyl groups into organic molecules are highly desirable. In the formation of fluoroalkyl cyclopropanes, the best results so far showed 75% ee (P. Le Maux, S. Julliard, G. Simoneaux Synthesis 2006, 1701). The Rh2(PTAD)4 catalyst system developed by Davies was unique in producing the chiral cyclopropane 3 in both high yield and enantioselectivity. Furthermore, a single diastereomer was observed. The nature of the aryl groups on the reacting partners did not have a significant impact on the enantioselectivity, except in the case of electron-rich alkenes (3a: 88% ee).