Premium
Chalcogeno Morita−Baylis−Hillman Reaction of 2‐(Methylchalcogeno)phenyl Vinyl Ketones with Aldehydes, Ketones, and α‐Dicarbonyl Compounds
Author(s) -
Kinoshita Hironori,
Kinoshita Sayaka,
Munechika Yukari,
Iwamura Tatsunori,
Watanabe Shinichi,
Kataoka Tadashi
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300546
Subject(s) - chemistry , baylis–hillman reaction , adduct , sulfonium , methyl vinyl ketone , organic chemistry , medicinal chemistry , ketone , reaction mechanism , salt (chemistry) , addition reaction , catalysis
Reactions of 2‐(methylchalcogeno)phenyl vinyl ketones 1 and 4 with aldehydes 5 were conducted in the presence of BF 3 ·Et 2 O. The reaction was quenched by addition of Et 3 N 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 NaHCO 3 , 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)