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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.