Abstract
| - Silylketene dithioacetal 1 reacted with aldehydes 2a−o, 14, or cinnamaldehyde (11) in the presenceof 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 orallylic alcohol 25, respectively, in rather low yields. The formation mechanisms of these productsare discussed.
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