Key Laboratory of Asymmetric Synthesis and Chirotechnology of Sichuan Province, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.
J Org Chem. 2012 Sep 21;77(18):8338-43. doi: 10.1021/jo301115t. Epub 2012 Sep 10.
The direct asymmetric vinylogous Mannich reaction of 3,4-dihalofuran-2(5H)-one with aldimine catalyzed by quinine was first reported, and γ-butenolides have been obtained in excellent yield (up to 98%) and enantioselectivities (up to 95% ee). The synthetic applications of this protocol are demonstrated in the preparations of γ-substituted amino butyrolactones and vicinal amino alcohols.
首次报道了奎宁催化的 3,4-二卤代呋喃-2(5H)-酮与亚胺的直接不对称乙烯基 Mannich 反应，得到了γ-丁内酯，产率高达 98%，对映选择性高达 95%ee。该方案的合成应用在γ-取代氨基丁内酯和邻氨基醇的制备中得到了展示。
