Journal
ORGANIC LETTERS
Volume 20, Issue 1, Pages 174-177Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03539
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Funding
- Thousand Plan Youth Program
- Fundamental Research Funds for the Central Universities
- East China University of Science and Technology
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An unprecedented chiral secondary amine-catalyzed formal [4 + 2] annulation of aldehydes and oxidation generated beta-unsubstituted o-QMs is reported. This asymmetric protocol allows direct functionalization of the benzylic C-H bonds and furnishes [4 + 2] cycloadducts, chromanols, with excellent enantioselectivity and in up to 92% yield. The usability of this approach was further demonstrated by the enantioselective synthesis of anticancer Rhinacanthins derivative NKPLS8.
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