Chemistry Letters

Dianions of N-monosubstituted-3-(phenylsulfonyl) propanamides. Convenient reagents for the synthesis of 5-alkyl-2 (5H)-furanones.

K Tanaka, H Wakita, H Yoda, A Kaji

Index: Tanaka, Kazuhiko; Wakita, Hisanori; Yoda, Hidemi; Kaji, Aritsune Chemistry Letters, 1984 , p. 1359 - 1362

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Citation Number: 17

Abstract

Treatment of N-phenyl-3-(phenylsulfonyl) propanamide with 2 equiv. of butyllithium at− 78° C afforded the dianion. Aldehydes and ketones upon treatment with the dianion provided stable γ-hydroxy amides, which were converted in good yields to 5-alkyl-2 (5H)-furanones. Optically active (R)-and (S)-5-octyl-2 (5H)-furanones, and (R)-and (S)-5-tridecyl-2 (5H)- furanones were prepared from aldehydes and the dianions, derived from chiral N- ...