A Catalytic Carbon–Phosphorus Ylide Reaction: Phosphane‐Catalyzed Annulation of Allylic Compounds with Electron‐Deficient Alkenes | Zendy

Du Yishu | Zendy; Lu Xiyan | Zendy; Zhang Chunming | Zendy

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A Catalytic Carbon–Phosphorus Ylide Reaction: Phosphane‐Catalyzed Annulation of Allylic Compounds with Electron‐Deficient Alkenes

Author(s) -

Du Yishu,

Lu Xiyan,

Zhang Chunming

Publication year - 2003

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200390266

Subject(s) - annulation , ylide , allylic rearrangement , chemistry , catalysis , bromide , medicinal chemistry , phosphorus , adduct , organic chemistry

Readily available starting materials and high selectivity : These are two appealing features of the phosphane‐catalyzed carbon–phosphorus ylide reaction described. Bromide, acetate, or tert ‐butyl carbonate derivatives of adducts formed by the Morita–Baylis–Hillman reaction react with PPh 3 to form an allylic ylide. Phosphane‐catalyzed annulation of the ylides with electron‐deficient alkenes results in the facile construction of cyclopentenes [Eq. (1)]. X=Br, OAc, OBoc; E=CO 2 Et.

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