Preparation of trans-2,5-disubstituted pyrrolidines by asymmetric iodocyclization of homoallylic amines

ORGN 693

Franklin A Davis, Minsoo Song, msong@temple.edu, and Alexander Augustine, alexaug@temple.edu. Department of Chemistry, Temple University, Philadelphia, PA 19122
Enantiopure trans-2,5-disubstituted pyrrolidines were prepared from homoallylic amines in the presence of I2 and K2CO3. Aliphatic, aromatic, and alkenyl groups were tolerated. Inseparable mixture of E and Z isomers of homoallylic amines were prepared from β-amino aldehydes and alkyltriphenylphosphonium bromides. E-olefininic homoallylic amines provided trans-2,5-disubstituted pyrrolidines selectively and Z-olefinic homoallylic amines were fully recovered from the iodocyclization reactions. Isomerization of Z-olefinic homoallylic amines to E-forms was developed as well.

 

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