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Two methods for the preparation of 2-cyclohexenones from resin-bound 1,3-cyclohexanedione

✍ Scribed by Mark E. Fraley; Robert S. Rubino

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 217 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00631-x

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✦ Synopsis

The addition of organolithium or Grignard reagents to vinylogous ester resin l followed by mild hydrolysis of product resins 2 provides 3-alkyl-2-cyclohexenones in high purity (>95%). Alternatively, conversion of 1 to vinyl triflate resin 4 followed by palladium-mediated couplings with aryl boronic acids and hydrolysis furnishes 3-aryl-2-cyclohexenones in lower yield, but exceptional purity.

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