Takagi Ryukichi, Fujii Emi, Kondo Hirotoshi
Department of Chemistry, Graduate School of Science , Hiroshima University , 1-3-1 Kagamiyama , Higashi-Hiroshima 739-8526 , Japan.
J Org Chem. 2018 Sep 21;83(18):11191-11203. doi: 10.1021/acs.joc.8b01777. Epub 2018 Aug 31.
This study aims to develop a highly enantioselective Michael reaction of cyclic β-ketoesters with Morita-Baylis-Hillman (MBH) derivatives using a phase-transfer catalyst. Cyclic β-ketoesters reacted with MBH derivatives to stereoselectively generate a quaternary carbon center in the presence of cinchona alkaloid-derived bulky ammonium catalyst, and aqueous KOH and Michael adducts bearing an acrylate moiety were obtained in good chemical yields with good enantioselectivity.
本研究旨在利用相转移催化剂开发环状β-酮酯与森田-贝利斯-希尔曼(MBH)衍生物的高度对映选择性迈克尔反应。在金鸡纳生物碱衍生的大体积铵催化剂存在下,环状β-酮酯与MBH衍生物反应,立体选择性地生成季碳中心,以良好的化学产率和对映选择性得到含丙烯酸酯部分的迈克尔加成物以及氢氧化钾水溶液。