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Lewis acid-promoted deoxygenative di[β,β-bis(ethylthio)]vinylation of aldehydes with trimethylsilylketene bis(ethylthio)acetal
Okauchi,Tanaka,Minami
, p. 3924 - 3929 (2007/10/03)
Silylketene dithioacetal 1 reacted with aldehydes 2a-o, 14, or cinnamaldehyde (11) in the presence of Lewis acid to give deoxygenative divinylation products, 3-substituted 1,4-pentadienes 3a-o, 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 22a-c or α-ketoester 24 led to tetrasubstituted furans 23a-c or allylic alcohol 25, respectively, in rather low yields. The formation mechanisms of these products are discussed.
