4.8 Article

Aminocatalytic Asymmetric exo-Diels-Alder Reaction with Methiodide Salts of Mannich Bases and 2,4-Dienals to Construct Chiral Spirocycles

Journal

ORGANIC LETTERS
Volume 15, Issue 4, Pages 968-971

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol4002015

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Funding

  1. NSFC [21125206, 21021001]
  2. National Basic Research Program of China (973 Program) [2010CB833300]

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An asymmetric exo-Diels-Alder reaction of alpha-methylene carbonyl compounds, generated In situ from stable methiodide salts of Mannich bases, with 2,4-dienals, has been developed through trienamine activation of a chiral secondary amine. A spectrum of spirocyclanes with high molecular complexity was efficiently constructed In moderate to excellent diastereo- and enantioselectivity.

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