期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 38, 页码 12333-12337出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807308
关键词
asymmetric catalysis; cycloaddition; dihydrofurans; fluorine; palladium
资金
- Swiss National Science Foundation [P300P2-171434]
- Swiss National Science Foundation (SNF) [P300P2_171434] Funding Source: Swiss National Science Foundation (SNF)
A nitrile-substituted trimethylenemethane (TMM) donor undergoes palladium-catalyzed [3+2] cycloadditions with fluorinated ketones to generate tetrasubstituted trifluoromethylated centers in high enantioselectivity under mild conditions. The generation of the palladium-TMM complex was achieved by a self-deprotonation strategy, which shows remarkable improvements in regiocontrol, efficiency, and atom economy of asymmetric [3+2] cycloadditions. Moreover, the versatility of the nitrile group provides direct access to a variety of synthetically useful intermediates, including amides, aldehydes, and esters. The developed reaction conditions allow for the synthesis of a wide variety of aromatic, heteroaromatic, and aliphatic fluorinated dihydrofurans in excellent regio- and enantioselectivities.
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