A simple enantioselective route toward (R)- and (S)-Rolipram via anhydride desymmetrization

作者：Ivsic Trpimir; Hamersak Zdenko^*

来源：Tetrahedron: Asymmetry , 2013, 24(4): 217-222.

DOI：10.1016/j.tetasy.2013.01.009

A highly enantioselective metal-free synthesis of both enantiomers of Rolipram is reported. The key stereoinductive step is a cinchona alkaloid catalyzed opening of a cyclic anhydride prepared from isovanillin, where both enantiomers are available using the same chiral catalyst in two protocols. An extended one-pot Curtius sequence provides the lactam directly from the desymmetrization product after enrichment in high yield and excellent ee.

• 出版日期2013-2-28