Zinc-Mediated Chain Extension of β-Keto Phosphonates
- 10 August 2000
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (18) , 5615-5622
- https://doi.org/10.1021/jo000343f
Abstract
A variety of β-keto phosphonates can be converted to γ-keto phosphonates through reaction with ethyl(iodomethyl)zinc. The presence of α-alkyl substituents, Lewis basic functionality, and modestly acidic NH-protons are accommodated in substrates of this reaction. Chain extension of β-keto phosphonates that contained olefinic functionality proceeded more quickly than cyclopropanation; however, it was not possible to effect the chain extension to the exclusion of cyclopropane formation. A primary reason for this imperfect chemoselectivity appears to be the slow chain extension of β-keto phosphonates. Nevertheless, the simplicity, the scope, and efficiency of this method serve to make it an attractive alternative to the established methods for γ-keto phosphonate formation.Keywords
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