P(RNCH(2)CH(2))(3)N-catalyzed 1,2-addition reactions of activated allylic synthons. |
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| Authors: | Philip B Kisanga John G Verkade |
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| Institution: | Department of Chemistry, Iowa State University, Ames, Iowa 50010, USA. |
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| Abstract: | Activated allylic compounds of the type RCH:CHCH(2)Z (Z = CN, CO(2)Me) react efficiently with aromatic aldehydes in the presence of 20-40 mol % of P(R'NCH(2)CH(2))(3)N at -94 to -63 degrees C. Both R = H and R = Me lead exclusively to alpha-addition products. When R = H and Z = CN, an allylic transposition occurs to afford a Baylis-Hillman product as the only product. |
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