Steric and electronic effects in the asymmetric hydroacylation reaction of o-alkenylbenzaldehydes

ORGN 781

Andrew T. Morehead Jr., moreheada@mail.ecu.edu and Avery Lamar Watkins, alw0330@mail.ecu.edu. Department of Chemistry, East Carolina University, 564 Science and Technology Building, Greenville, NC 27858
We have discovered that the intramolecular hydroacylation reaction of substituted ortho-alkenylbenzaldehydes with [BINAPRh]+ gives the corresponding 3-substituted indanones with excellent yields and high enantiomeric excess (Equation 1). The subtle interaction between steric and electronic effects and their effect on the enantiomeric excess will be discussed.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005