Asymmetric epoxidation, Michael addition, and triple cascade reaction using polymer-supported prolinol-based auxiliaries |
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Authors: | Michael C. Varela Kit S. Lam |
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Affiliation: | a Department of Chemistry, University of California, One Shields Avenue, Davis, CA 95616, United States b Division of Hematology and Oncology, UC Davis Cancer Center, 4501 X Street, Sacramento, CA 95817, United States |
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Abstract: | The applicability of polymer-supported diphenylprolinol derivatives in directing either asymmetric epoxidation or Michael addition of suitable α,β-unsaturated substrates has been assessed. Epoxidation of cinnamaldehyde in the solid state give poorer yields and stereoselectivities than in the solution-phase systems. In contrast Michael additions of several aldehyde enolates to 2-nitro-1-arylalkenes gave results that approached or surpassed those in solution, and could be extended successfully to a three-component Michael/Michael/aldol cascade process. Comparisons of the results of pendant- versus crosslinked functionalized resins in these applications were revealing of the benefits and limitations of each, as were attempts to reuse the polymer-bound auxiliaries. |
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Keywords: | Crosslinking monomer Diphenylprolinol Enantioselective epoxidation Enantioselective Michael addition Triple cascade reaction Polymer beads |
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