PhCHP(MeNCH2CH2)3N: A Novel Ylide for QuantitativeESelectivity in the Wittig Reaction
- 26 April 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (10) , 3521-3524
- https://doi.org/10.1021/jo0100704
Abstract
PhCHP(MeNCH2CH2)3N (1), a semi-stabilized ylide prepared from the commercially available nonionic base P(MeNCH2CH2)3N, 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.Keywords
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