Bulletin of the Chemical Society of Japan p. 2339 - 2347 (1993)
Update date:2022-07-30
Topics:
Satoh, Tsuyoshi
Oguro, Kazuko
Shishikura, Jun-ichi
Kanetaka, Naomi
Okada, Reiko
Yamakawa, Koji
A method for synthesizing carboxylic acids and their derivatives from aldehydes and ketones via α-chloro-α-sulfonyl ketones is described.Acyclic α-chloro-α-sulfonyl ketones were synthesized from aldehydes and 1-chloroalkyl p-tolyl sulfoxides with carbon-carbon coupling in good overall yields.Cyclic α-chloro-α-sulfonyl ketones were synthesized from cyclic ketones in three steps in high overall yields.The Favorskii rearrangement of both acyclic and cyclic α-chloro-α-sulfonyl ketones with sodium hydride in the presence of amine gave β-sulfonyl amides with skeletal rearrangement in good to excellent yield.Amides and α,β-unsaturated amides were synthesized from the β-sulfonyl amides.Treatment of the cyclic α-chloro-α-sulfonyl ketones with alkoxides and hydroxide gave carboxylic esters and acids with cleavage of the ring in good to excellent yields.
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