期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 35, 页码 11408-11412出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201806249
关键词
asymmetric catalysis; chiral butenolides; enantioselectivity; fluorine; zinc
资金
- National Science Foundation [CHE-1360634]
- National Institute of Health [GM-033049]
- DAAD
We report a Zn-ProPhenol catalyzed asymmetric Mannich reaction between butenolides and polyfluorinated alkynyl ketimines to obtain vinylogous products featuring two contiguous tetrasubstituted stereogenic centers. Notably, this is the first successful use of ketimines in the ProPhenol Mannich process, and the reaction offers a new approach for the preparation of pharmaceutically relevant products possessing trifluoromethylated tetrasubstituted alkylamines. The reaction can be performed on large scale with reduced catalyst loading without impacting its efficiency. Moreover, the acetylene moiety can be further elaborated using various methods.
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