Kisanga Philip B, Verkade John G
Department of Chemistry, Iowa State University, Ames, Iowa 50010, USA.
J Org Chem. 2002 Jan 25;67(2):426-30. doi: 10.1021/jo0106492.
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.
CHCH(2)Z（Z = CN、CO(2)Me）类型的活化烯丙基化合物在20 - 40摩尔%的P(R'NCH(2)CH(2))(3)N存在下，于-94至-63摄氏度时能与芳香醛高效反应。R = H和R = Me时均仅生成α-加成产物。当R = H且Z = CN时，会发生烯丙基重排，得到唯一产物即贝利斯-希尔曼产物。
