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Intramolecular charge–charge repulsion rather than traditional steric control is responsible for the high diastereoselectivity (up to 94 % de) obtained in tBuOK-induced difluoromethylenation of aldehydes 1 with difluoromethyl phenyl sulfone (2) to give symmetrical and unsymmetrical anti-2,2-difluoropropane-1,3-diols 3.
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Prakash et al. (2003) studied this question.
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