Asymmetric Diels-Alder reaction catalyzed by novel hydrazine organocatalysts

ORGN 584

Gregory R. Cook, Gregory.Cook@ndsu.edu, Yoko Takahashi, yoko.takahashi@ndsu.edu, and Santosh Bhor, santosh.bhor@ndsu.edu. Department of Chemistry and Molecular Biology, North Dakota State University, 1231 Albrecht Avenue, P.O. Box 5516, Fargo, ND 58105-5516
Methods based on metal-free organic catalysts have attracted great attention recently due to their stability under aerobic wet conditions. Organocatalysts are relatively inexpensive and do not cause metal contamination. The Diels-Alder reaction remains one of the most powerful tools in the construction of a wide variety of natural products. Stereoselective Diels-Alder reaction with cyclopentadiene with ?,?-unsaturated carbonyl compounds such as acrolein, methyl vinyl ketone, and methyl acrylate is known to give mainly endo cycloadducts, which is the predominant products in many of the Diels Alder reaction. We have found novel acyclic hydrazine organocatalysts that gives access to both the endo and exo cycloadducts with high enantioselectivity. Details of our investigation and improvements thereafter will be presented.

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 20, 2007 BCEC -- Exhibit Hall - B2, Sci-Mix

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007