文献类型：期刊文献

英文题名：Exploiting Distal Reactivity of Coumarins: A Rhodium-Catalyzed Vinylogous Asymmetric Ring-Opening Reaction

作者：Loh, Charles C. J.[1];Schmid, Matthias[1];Peters, Brendan[1];Fang, Xiang[1,2,3];Lautens, Mark[1]

机构：[1]Univ Toronto, Dept Chem, Davenport Chem Labs, 80 St George St, Toronto, ON M5S 3H6, Canada;[2]E China Univ Sci & Technol, Sch Chem & Mol Engn, Adv Mat Lab, 130 Meilong Rd, Shanghai 200237, Peoples R China;[3]E China Univ Sci & Technol, Sch Chem & Mol Engn, Inst Fine Chem, 130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2016

卷号：55

期号：14

起止页码：4600

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20161002077581);WOS:【SCI-EXPANDED(收录号:WOS:000373133000035)，CCR-EXPANDED(收录号:WOS:000373133000035)】；

基金：We thank Solvias AG, Umicore, and Johnson Matthey for the generous donation of ligands and rhodium catalysts. The National Sciences and Engineering Research Council (NSERC) is gratefully acknowledged for financial support. C.C.J.L. thanks the Deutsche Forschungsgemeinschaft (DFG) for a postdoctoral fellowship (LO 2065/1-1). B.P. thanks NSERC for graduate funding. F.X. thanks the National Natural Science Foundation of China (Nos. 21172148, 21202044) and China Scholarship Council (Nos. 201306745008) for funding. Dr. Alan Lough (University of Toronto) is gratefully acknowledged for single crystal X-ray analysis.

语种：英文

外文关键词：enantioselectivity; heterocycles; ring-opening reactions; rhodium; synthetic methods

摘要：While the utility of vinylogous enolates is well established in the setting of vinylogous aldol, Mannich, and Michael chemistries, literature reports concerning -reactivity are scarce for other reaction classes. Presented herein is an unprecedented example of vinylogous reactivity exemplified by the rhodium-catalyzed asymmetric ring-opening reaction of oxabicycles. This strategy also provides a powerful route to incorporate the biologically useful coumarin motif into the hydronapthalene scaffold.