Stereoselective Michael-aldol tandem reaction of phenylselenomagnesium bromide with acetylenic sulfones and aldehydes. An efficient synthesis of polyfunctionalized allylic alcohols.
A mixture of phenylselenomagnesium bromide, an acetylenic sulfone, and an aldehyde in THF/CH(2)Cl(2) afforded Michael-aldol tandem adduct, i.e., (Z)-beta-phenylseleno-alpha-(p-tolylsulfonyl)allylic alcohol, in good yield with high stereoselectivity. The stereoselectivity greatly depended on solvent. [reaction: see text]
Huang
Xian
X
Department of Chemistry, Zhejiang University, Xi-xi Campus, Hangzhou 310028, P. R. China. huangx@mail.hz.zj.cn
Xie
Meihua
M