397872-34-3Relevant academic research and scientific papers
Self-assisted tandem Michael-aldol reactions of α,β-unsaturated ketones with aldehydes
Kataoka,Kinoshita,Kinoshita,Fujita,Iwamura,Watanabe
, p. 1958 - 1959 (2001)
The tandem Michael-aldol reaction of 1-[2-(methylsulfanyl)phenyl]prop-2-en-1-one (1) or the seleno congener 4 with p-nitrobenzaldehyde in the presence of BF3,Et2O gave the Baylis-Hillman adduct 2 or 5 and onium salt 3 or 6, respectiv
Chalcogeno Morita-Baylis-Hillman Reaction of 2-(Methylchalcogeno)phenyl Vinyl Ketones with Aldehydes, Ketones, and α-Dicarbonyl Compounds
Kinoshita, Hironori,Kinoshita, Sayaka,Munechika, Yukari,Iwamura, Tatsunori,Watanabe, Shin-Ichi,Kataoka, Tadashi
, p. 4852 - 4861 (2007/10/03)
Reactions of 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 with aldehydes 5 were conducted in the presence of BF3·Et 2O. The reaction was quenched by addition of Et3N and gave the Morita-Baylis-Hillman adducts 6-7 in good yields. When the reaction mixture of 1 with 5a was worked up with saturated aqueous NaHCO3, the sulfonium salt 8a was obtained together with 6. Ketones 10, α-diketones, and α-oxo esters 13, which hardly react in the traditional Morita-Baylis-Hillman reaction, similarly reacted with 2-(methylchalcogeno)phenyl vinyl ketones 1 and 4 to give the Morita-Baylis-Hillman adducts 11-12 and 14-15. Selenochromanones 9 and 16 were obtained together with 7 and 15 from reactions of seleno derivative 4, with 5 and 13 as by-products. The formation mechanism for the sulfonium salt syn-trans-8a is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
