posted on 2001-05-03, 00:00authored byTatsuo Okauchi, Tatsuyoshi Tanaka, Toru Minami
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.