C-chiral organolithium reagents are useful carbon nucleophiles; the corresponding Grignard reagents have received considerably less study. To date Mg/X exchange is the only successful route to highly enantioenriched ?C-chiral Grignard reagents, and we used this method to prepare Grignard reagents 1  and ?trans?-2 .?  Configurational stability of these compounds is much greater in Et?2?O than in 2-MeTHF and THF. In this paper we will present a detailed kinetic studies of the racemization/epimerization of these reagents and present a mechanism that accounts for the role of solvent.

<i>?C</i>-chiral Grignard reagents: How do they racemize?

246th National Meeting (2013)

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?C-chiral Grignard reagents: How do they racemize?