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The Grignard reagent 6, in which the magnesium-bearing carbon atom is the sole stereogenic centre has been added to CO2, PhNCO, PhNCS and certain aldehydes with full retention of configuration. Reaction with benzophenone, electron-deficient aldehydes and several allyl halides proceeded with partial or complete racemization. The findings are discussed with respect to a dichotomy between concerted polar and stepwise SET reaction pathways.
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Hoffmann et al. (2001) studied this question.
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