期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 3, 页码 885-888出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611214
关键词
asymmetric catalysis; Claisen rearrangement; gold; hydroalkoxylation; nickel
资金
- National Natural Science Foundation of China [21372162, 21321061, 21432006]
A highly efficient asymmetric cascade reaction between alkynyl esters and allylic alcohols has been realized. Key to success was the combination of a hydroalkoxylation reaction catalyzed by a pi-acidic gold(I) complex witha Claisen rearrangement catalyzed by a chiral Lewis acidic N,N'-dioxide-nickel(II) complex. A range of acyclic alpha-allyl beta-keto esters were synthesized in high yields (up to 99%) with good diastereoselectivities (up to 97:3) and excellent enantioselectivities (up to 99% ee) under mild reaction conditions. These products can be easily transformed into optically active beta-hydroxy esters, beta-hydroxy acids, or 1,3-diols.
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