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An efficient and practical synthesis of diphenyl cyanomethylenephosphonate: Applications to the stereoselective synthesis of cis-α,β-unsaturated nitriles

✍ Scribed by Tony Y. Zhang; John C. O'Toole; James M. Dunigan

Book ID: 104258684
Publisher: Elsevier Science
Year: 1998
Tongue: French
Weight: 175 KB
Volume: 39
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)10836-x

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✦ Synopsis

Diphenyl cyanomethylenephosphonate (PhO)2POCH2CN was prepared as a stable crystalline solid in high yield in a single step from acetonitrile, LDA, and (PhO)2P(O)C1. The potassium ylide generated from this compound afforded o;//-unsaturated nitriles upon reacting with aldehydes, with a stereoselectivity of 64-100% favoring the cis-isomer.

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