A Green Chemistry Approach to a More Efficient Asymmetric Catalyst: Solvent-Free and Highly Concentrated Alkyl Additions to Ketones
Sang-Jin Jeon, Hongmei Li and Patrick J. Walsh*
*Department of Chemistry, P. Roy and Diana T. Vagelos Laboratories, University of Pennsylvania, Philadelphia, Pennsylvania 19104, Email: pwalshsas.upenn.edu
S.-J. Jeon, H. Li, P. J. Walsh, J. Am. Chem. Soc., 2005, 127, 16416-16425.
DOI: 10.1021/ja052200m
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Abstract
The catalytic asymmetric addition of alkyl groups to ketones under highly concentrated and solvent-free conditions permits reduction in catalyst loading by a factor of 2- to 40-fold compared with standard reaction conditions employing toluene and hexanes. Using cyclic conjugated enones, solvent-free asymmetric addition followed by a diastereoselective epoxidation using 5.5 M decane solution of tert-butyl hydroperoxide generated epoxy alcohols.
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S.-J. Jeon, P. J. Walsh, J. Am. Chem. Soc., 2003, 125, 9544-9545.
C. Garcia, P. J. Walsh, Org. Lett., 2003, 5, 3641-3644.
Key Words
1,2-addition, epoxidation, tert-butyl hydroperoxide, green chemistry
ID: J48-Y2005-2750