4.7 Article

Efficient synthesis of optically active 4-nitro-cyclohexanones via bifunctional thiourea-base catalyzed double-Michael addition of nitromethane to dienones

Journal

CHEMICAL COMMUNICATIONS
Volume 47, Issue 13, Pages 3992-3994

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c0cc05418f

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Funding

  1. National Natural Science Foundation of China [21072145]
  2. Foundation for the Author of National Excellent Doctoral Dissertation of PR China [200931]
  3. Natural Science Foundation of Jiangsu Province of China [BK2009115]

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Thiourea-modified cinchona alkaloids as bifunctional catalysts and a base could catalyze a stepwise [5+1] cyclization of divinyl ketones with nitromethane via double Michael additions, furnishing optically active 4-nitro-cyclohexanones with good yields, excellent diastereoselectivities (>20 : 1) and high enantiomeric ratios (up to 97 : 3).

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