Stereodivergent cascade imine ® azomethine ylide ® 1,3-dipolar cycloadditive approach to ƒ¿-chiral pyrrolidines

ORGN 662

Philip Garner, ppg@case.edu and H. Ümit Kaniskan, huk@case.edu. Department of Chemistry, Case Western Reserve University, 10900 Euclid Ave, Cleveland, OH 44106
Stereodivergent [3+2] cycloadditions of chiral α-amino azomethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and α-stereocenters. The latter result forms the basis for a new synthetic approach to the naphthyridinomycin family of antitumor antibiotics.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005