期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 53, 期 48, 页码 13229-13233出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201408364
关键词
annulation; asymmetric catalysis; carbenes; cyclopentenones; nickel
资金
- Swiss National Science Foundation [137666]
Cyclopentenones are versatile structural motifs of natural products as well as reactive synthetic intermediates. The nickel-catalyzed reductive [3+2] cycloaddition of alpha,beta-unsaturated aromatic esters and alkynes constitutes an efficient method for their synthesis. Here, nickel(0) catalysts comprising a chiral bulky C-1-symmetric N-heterocyclic carbene ligand were shown to enable an efficient asymmetric synthesis of cyclopentenones from mesityl enoates and internal alkynes under mild conditions. The bulky NHC ligand provided the cyclopentenone products in very high enantioselectivity and led to a regioselective incorporation of unsymmetrically substituted alkynes.
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