Optimization of the Catalytic Asymmetric Addition of Nitroalkanes to Cyclic Enones with trans-4,5-Methano-l-proline

Stephen Hanessian,* Zhihui Shao, and Jayakumar S. Warrier
Department of Chemistry, Universit de Montral, P.O. Box 6128, Station Centre-ville, Montral, QC H3C 3J7, Canada
Org. Lett., 2006, 8 (21), pp 4787–4790
DOI: 10.1021/ol0618407
Publication Date (Web): September 19, 2006
Copyright © 2006 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.

, stephen.hanessian@umontreal.ca

Abstract

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The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-l-proline proceeds with >99% ee and excellent chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities. Proline hydroxamic acid and its trans-4,5-methano -l-proline hydroxamic acid are also effective organocatalysts in the addition of 2-nitropropane to 2-cyclohexenone (75% and 81% ee, respectively).

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History

  • Published In Issue October 12, 2006
  • Received July 25, 2006

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