Titanium as a regio- and stereo-selective control element in the reaction of α-alkoxyallylic phosphine oxide anions with carbonyl compounds
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 5,p. 1039-1046
- https://doi.org/10.1039/p19880001039
Abstract
A general method is described for directing the condensation of α-methoxyallylphosphine oxide anions (2) with aldehydes, preferentially at the α-position of the allyl system. The procedure, which employs the formation of the titanium ate complex, yields pure diastereoisomers with high stereoselectivity, and these can be used in Horner-Wittig reactions to provide an efficient and convenient synthesis of conjugated methoxydienes of defined geometry. Under the same conditions, acyl halides yield γ-adducts.Keywords
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