Toward the development of an asymmetric Morita-Baylis-Hillman reaction

ORGN 696

Yun-Ming Lin, and Julie Boucau, jboucau@UTNet.UToledo.Edu. Department of Chemistry, University of Toledo, 2801 W. Bancroft St., Toledo, OH 43606
The asymmetric Morita-Baylis-Hillman (MBH) reaction has the potential to become an efficient and atom economical organic transformation. However, the synthetic applications of this reaction are hampered due to its current limitations (slow reaction rates, etc.) and the lack of a generally applicable catalytic asymmetric method. We envision a novel bifunctional Lewis acid-Lewis base (LA-LB) catalytic system as a new approach for its improvement. We covalently attached chiral Lewis bases to privileged ligand frameworks to produce a novel class of mixed ligands. Chelation of these hemilable ligands to metals gave new complexes that would activate both the electrophile and the latent nucleophile in the MBH reaction to give rise to rate acceleration. Herein, our research effort toward the development of an asymmetric MBH reaction will be discussed.

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

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