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Synthesis of Cyclopentenones from Cyclopropanes and Silyl Ynol Ethers
Author(s) -
Qi Xiangbing,
Ready Joseph M.
Publication year - 2008
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.200801957
Subject(s) - library science , citation , medicine , computer science
Exploiting an opening: Lewis acid promoted ring‐opening of donor–acceptor cyclopropanes generates a 1,3‐zwitterion; cycloaddition with a silyl ynol ether leads to a general synthesis of cyclopentenones (see scheme). Substitution is tolerated on the ynol and on all positions of the cyclopropane to give tri‐, tetra‐, and penta‐substituted cyclopentenones in high yield.