Communication

A Three-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones

  1. Zhenghu Xu Dr.1,
  2. Tyler Buechler1,
  3. Kraig Wheeler Prof.2,
  4. Hong Wang Prof.1

Article first published online: 11 FEB 2010

DOI: 10.1002/chem.200903508

Issue

Chemistry - A European Journal

Chemistry - A European Journal

Volume 16, Issue 10, pages 2972–2976, March 8, 2010

Additional Information

How to Cite

Xu, Z., Buechler, T., Wheeler, K. and Wang, H. (2010), A Three-Component Reaction Based on a Remote-Group-Directed Dynamic Kinetic Aza-Michael Addition: Stereoselective Synthesis of Imidazolidin-4-ones. Chem. Eur. J., 16: 2972–2976. doi: 10.1002/chem.200903508

Author Information

  1. 1

    Department of Chemistry and Biochemistry, Miami University, 701 East High Street, Oxford, OH 45056 (USA), Fax: (+1) 513 529-5715

  2. 2

    Department of Chemistry, Eastern Illinois University, 600 Lincoln Ave., Charleston, IL 61920 (USA)

Publication History

  1. Issue published online: 1 MAR 2010
  2. Article first published online: 11 FEB 2010
  3. Manuscript Received: 21 DEC 2009

Funded by

  • NSF. Grant Number: 0722547

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Keywords:

  • Brønsted acid catalysis;
  • diastereoselectivity;
  • dynamic kinetic alkylation;
  • Michael addition;
  • multicomponent reactions
Thumbnail image of graphical abstract

In control: An α-amino amide reacted with an aldehyde and a Michael acceptor to form stable imidazolidin-4-ones with high stereoselectivity. A dynamic kinetic aza-Michael addition was discovered and applied to the three-component reaction to enforce high stereoselectivity. A remote group was incorporated to invert the reaction process and direct the reaction towards the desired product (see scheme).

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