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, Université de Montréal, P.O. Box 6128, Station
Centre-ville, Montréal, QC H3C 3J7, Canada, Email: stephen.hanessian
umontreal.ca
S. Hanessian, Z. Shao, J. S. Warrier, Org. Lett., 2006, 8, 4787-4790.
DOI: 10.1021/ol0618407
see article for more reactions
Abstract
The conjugate addition of symmetrical 2-nitroalkanes to 2-cycloalkenones catalyzed by trans-4,5-methano-L-proline proceeds with excellent enantioselectivity and chemical yields. 1-Nitroalkanes afford diastereomeric syn/anti products that can be separated with good individual enantioselectivities.
see article for more examples
Key Words
Michael Addition, Organocatalysis, Nitro Compounds
ID: J54-Y2006-3210
