4.8 Article

Enantioselective N-Heterocyclic Carbene-Catalyzed Michael Addition to α,β-Unsaturated Aldehydes by Redox Oxidation

Journal

ORGANIC LETTERS
Volume 13, Issue 15, Pages 4080-4083

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol201595f

Keywords

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Funding

  1. National Natural Science Foundation of China [20732006, 20821002, 20972177, 21025209]
  2. National Basic Research Program of China (973 Program) [2009CB825300]

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Enantioselective N-heterocyclic carbene-catalyzed Michael addition reactions to alpha,beta-unsaturated aldehydes by redox oxidation were realized. With 10 mol % of camphor-derived triazolium salt D, 15 mol % of DBU, 5 mol % of NaBF4, and 100 mol % of quinone oxidant, the reactions of various dicarbonyl compounds with alpha,beta-unsaturated aldehydes led to 3,4-dihydro-alpha-pyrones in good yields and excellent ee's.

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