Paper
THE REACTION OF 3-METHYL-2-BUTENYL PHENYL SULFIDE WITH ALDEHYDES AND KETONES. APPLICATION TO THE SYNTHESIS OF 2,2-DIMETHYLCYCLOPROPANECARBALDEHYDES
Published Nov 5, 1974 · K. Kondo, K. Matsui, A. Negishi
Chemistry Letters
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Abstract
The base promoted addition of 3-methyl-2-butenyl phenyl sulfide to aldehydes and ketones occurred selectively on the γ-position of the allylic moiety. The product was converted to the methanesulfonate. Treatment of the resulting homoallylic ester with nucleophiles induced the cyclization to give cyclopropane derivatives in excellent yields.
3-Methyl-2-Butenyl Phenyl SULFIDE selectively adds to aldehydes and ketones, resulting in the synthesis of 2,2-DIMETHYLCYCLOPROPANECARBALDEHYDES in excellent yields.
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