The Journal of Organic Chemistry

Geminal acylation of ketones mediated by boron trichloride. An improved method for the synthesis of 4, 4-dimethyl-1, 3-cyclopentanediones

SN Crane, DJ Burnell

Index: Crane, Sheldon N.; Burnell, D. Jean Journal of Organic Chemistry, 1998 , vol. 63, # 16 p. 5708 - 5710

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Citation Number: 19

Abstract

The geminal acylation of acetals and ketones with 1, 2-bis [(trimethylsilyl) oxy] cyclobutene (1) catalyzed by BF3 ‚Et2O is a powerful method for the introduction of a 1, 3- cyclopentanedione moiety. 1 The process involves an initial aldol reaction that gives an isolable cyclobutanone compound, followed by an acid-induced acyl migration to provide the diketone. Both steps are now normally accomplished in one pot. 1b-d We showed that ...