Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis
Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis
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DOI：
10.1002/anie.201607788
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发表时间：
2016-12-05
影响因子：
16.6
通讯作者：
Jorgensen, Karl Anker
中科院分区：
文献类型：
--
作者：
Leth, Lars A.;Glaus, Florian;Jorgensen, Karl Anker
A novel reaction based on synergistic catalysis, combining palladium- and organocatalysis has been developed. The palladium catalyst activates vinyl benzoxazinanones via a decarboxylation to undergo a [4+2] cycloaddition with iminium-ion activated ,-unsaturated aldehydes. The reaction is demonstrated to proceed for a number of combinations of vinyl benzoxazinanones reacting with ,-unsaturated aldehydes, providing highly substituted vinyl tetrahydroquinolines in good to high yields, and excellent enantio- and diastereoselectivities (>98% ee and >20:1 d.r.). The palladium catalyst used in the synergistic catalysis can be re-used in a one-pot sequential coupling reaction with an aromatic boronic acid forming the coupling product in 95% yield, >20:1 d.r. and 99% ee.
