4.7 Article

The Application of a Recyclable Organocatalytic System to the Asymmetric Domino Michael/Henry Reaction in Aqueous Media

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 16, Pages 2905-2909

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100395

Keywords

asymmetric catalysis; catalyst recycling; domino reactions; Henry reaction; Michael addition

Funding

  1. Robert A. Welch Foundation [T-1460]
  2. Direct For Mathematical & Physical Scien
  3. Division Of Chemistry [0851966] Funding Source: National Science Foundation

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A new type of pyrrolidine-based organocatalyst has been developed and found to be very effective for the domino Michael/Henry reaction in aqueous solvents. For the reaction involving pentane-1,5-dial and various nitroolefins, good yields (6585%) and excellent enantioselectivities (99%) were obtained using this catalyst. In addition, the catalyst could be recycled up to four times resulting in good yields and up to seven times with good enantioselectivity.

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