American Chemical Society
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Lewis Acid-Promoted Deoxygenative Di[β,β-bis(ethylthio)]vinylation of Aldehydes with Trimethylsilylketene Bis(ethylthio)acetal

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journal contribution
posted on 2001-05-03, 00:00 authored by Tatsuo Okauchi, Tatsuyoshi Tanaka, Toru Minami
Silylketene dithioacetal 1 reacted with aldehydes 2ao, 14, or cinnamaldehyde (11) in the presence of Lewis acid to give deoxygenative divinylation products, 3-substituted 1,4-pentadienes 3ao, 15, or 5-phenyl-1,3,6-heptatriene 13b, in good to moderate yields. Similar reaction with 2-aminobenzaldehyde (16) or salicylaldehyde (17) produced quinoline 19 or chroman 20 in 40−58% yield. Treatment of 1 with α-diketones 22ac or α-ketoester 24 led to tetrasubstituted furans 23ac or allylic alcohol 25, respectively, in rather low yields. The formation mechanisms of these products are discussed.