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PhCH=P[MeNCH(2)CH(2)](3)N (1), a semi-stabilized ylide prepared from the commercially available nonionic base P[MeNCH(2)CH(2)](3)N, reacts with aldehydes to give alkenes in high yield with quantitative E selectivity. In contrast with other ylides, this E selectivity is maintained despite changes in the metal ion of the ionic base used to deprotonate 1, temperature, and solvent polarity. In conjunction with structural parameters gained from the X-ray molecular structure of 1, the pathway to E selectivity in these reactions is rationalized by the Vedejs model of Wittig reaction stereochemistry.
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Wang et al. (2001) studied this question.
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