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Synthesis of Trifluoromethyl-Substituted Cyclopropanes
J. R. Denton, D. Sukumaran, H. M. L. Davies*
The State University of New York at Buffalo, USA
23 August 2007 (online)
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).