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

DOI: 10.1016/S0040-4039(97)10836-X

Source and publish data:

Tetrahedron Letters p. 1461 - 1464 (1998)

Update date:2022-08-11

Topics:

Authors:

Zhang, Tony Y.

O'Toole, John C.

Dunigan, James M.

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Article abstract of DOI:10.1016/S0040-4039(97)10836-X

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)CI. The potassium ylide generated from this compound afforded α,β-unsaturated nitriles upon reacting with aldehydes, with a stereoselectivity of 64-100% favoring the cis-isomer.

Full text of DOI:10.1016/S0040-4039(97)10836-X

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