烯酮与缩醛的硫属元素-森田-贝利斯-希尔曼反应：烯酮简单的α-烷氧基烷基化反应

Chalcogeno-Morita-Baylis-Hillman reaction of enones with acetals: simple alpha-alkoxyalkylation of enones.

作者信息

Kinoshita Hironori, Osamura Takashi, Kinoshita Sayaka, Iwamura Tatsunori, Watanabe Shin-Ichi, Kataoka Tadashi, Tanabe Genzoh, Muraoka Osamu

机构信息

Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan.

出版信息

J Org Chem. 2003 Sep 19;68(19):7532-4. doi: 10.1021/jo0348470.

DOI:10.1021/jo0348470

PMID:12968914

Abstract

1-[2-(Methylsulfanyl)phenyl]prop-2-en-1-one (1) and the seleno congener (2) reacted with acetals 3 and 21 in the presence of BF(3).Et(2)O to give alpha-alkoxyalkyl enones 4, 5 and 22, 23 in good yields. When the reaction mixtures were worked up with a saturated NaHCO(3) solution instead of Et(3)N, onium salts 6 and 7 were obtained together with 4 and 5. Reactions with cyclic acetal 14 gave alpha-(beta-hydroxyethoxy) enones 15 and 16 accompanied by dimeric products 17 and 18.

摘要

1-[2-(甲硫基)苯基]丙-2-烯-1-酮(1)及其硒类似物(2)在BF(3)·Et(2)O存在下与缩醛3和21反应，以良好的产率得到α-烷氧基烷基烯酮4、5以及22、23。当反应混合物用饱和NaHCO(3)溶液而非Et(3)N进行后处理时，得到了鎓盐6和7以及4和5。与环状缩醛14的反应生成了α-(β-羟基乙氧基)烯酮15和16，并伴有二聚产物17和18。