期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 7, 页码 2392-2396出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201509247
关键词
ortho-quinone methides; oxonium ylides; phosphoric acids; rhodium; synergistic catalysis
资金
- DFG
We report herein a powerful and highly stereoselective protocol for the domino-type reaction of diazoesters with ortho-quinone methides generated in situ to furnish densely functionalized chromans with three contiguous stereogenic centers. A transition-metal and a Bronsted acid catalyst were shown to act synergistically to produce a transient oxonium ylide and ortho-quinone methide, respectively, in two distinct cycles. These intermediates underwent subsequent coupling in a conjugate-addition-hemiacetalization event in generally good yield with excellent diastereo-and enantioselectivity.
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