4.8 Article

N-Heterocyclic Carbene (NHC)-Catalyzed Highly Diastereo- and Enantioselective Oxo-Diels-Alder Reactions for Synthesis of Fused Pyrano[2,3-b]indoles

Journal

ORGANIC LETTERS
Volume 14, Issue 11, Pages 2894-2897

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol301175z

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Funding

  1. Hangzhou Normal University
  2. MOE in Singapore (ARC) [T206B3225]

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A chiral N-heterocyclic carbene (NHC)-catalyzed Diels-Alder reaction of 2-oxoindolin-3-ylidenes and alpha-chloroaldehydes was developed for the synthesis of fused pyrano[2,3-b]indoles in good to excellent yields (up to 99%) with high cis-diastereoselectivities (>99:1 dr) and enantioselectivities (up to >99% ee).

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