Tetrahedron p. 12955 - 12962 (1995)
Update date:2022-08-05
Topics:
Booker-Milburn
Thompson
Conjugate addition of a variety of Grignard reagents to 2-cyclopentenone gave a number of silyl enol ethers (1) which were treated with Et2Zn/CH2I2 to give the corresponding cyclopropyl silyl ethers (2) in good yield. Ferric chloride ring expansion followed by base elimination of the resulting β-chloro ketones gave the 4-substituted-2-cyclohexenones (4) in moderate to good overall yield. The overall process provides a convenient three step route to these enones from 2-cyclopentenone.
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