Microwave-Assisted Tandem Cross Metathesis Intramolecular Aza-Michael Reaction:  An Easy Entry to Cyclic β-Amino Carbonyl Derivatives

Santos Fustero,*†‡ Diego Jiménez,† María Sánchez-Roselló,† and Carlos del Pozo†
Departamento de Qumica Orgnica, Universidad de Valencia, E-46100 Burjassot, Spain, and Laboratorio de Molculas Orgnicas, Centro de Investigacin Prncipe Felipe, E-46013 Valencia, Spain
J. Am. Chem. Soc., 2007, 129 (21), pp 6700–6701
DOI: 10.1021/ja0709829
Publication Date (Web): May 5, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Universidad de Valencia.

,
‡

 Centro de Investigación Príncipe Felipe.

, santos.fustero@uv.es

Abstract

Abstract Image

Hoveyda−Grubbs catalyst in combination with BF3·OEt2 efficiently promotes tandem cross metathesis intramolecular aza-Michael reaction between enones and unsaturated carbamates resulting in the creation of β-amino carbonyl units. The use of microwave irradiation dramatically accelerates the process, enhancing the synthetic utility of this methodology for the preparation of these types of derivatives. When enantiomerically enriched α-branched amines were used as starting materials, the process was also very efficient, although with modest selectivity in the newly created stereocenter. The use of microwave irradiation led to an interesting effect, inverting the selectivity in the addition process.

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History

  • Published In Issue May 30, 2007
  • Received February 11, 2007

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