Silyl Ketene Acetal Chemistry: Steric Limitations in Lewis Acid-Promoted Addition of Ketones

G Wenke, EN Jacobsen, GE Totten…

Index: Wenke, G.; Jacobsen, E. N.; Totten, G. E.; Karydas, A. C.; Rhodes, Y. E. Synthetic Communications, 1983 , vol. 13, # 6 p. 449 - 458

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Citation Number: 13

Abstract

Lewis acid-promoted additions of ketones tosilyl ketene acetals is limited sterically with a-branched alkyl groups in the ketone. Cyclic ketones give high yields. Titanium, ferric and aluminum chlorides are effective catalysts. ... As a potential route to preparation of a variety of hindered ... 6-hydroxy esters to be utilized for synthesis of substituted ... Si'lyl ketene acetals are readily prepared2 and reactions may ... Although there have been numerous studies of analogous use of

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