Chiral benzimidazoline-2-ylidene Pd(II) complex for intermolecular asymmetric oxidative Heck-type reaction of arylboronic acids with alkenes

ORGN 523

Satoshi Sakaguchi, satoshi@ipcku.kansai-u.ac.jp, Kyung Soo Yoo, kyungsoo@usc.edu, Chan Phil Park, cksfeel@kaist.ac.kr, Justin O'Neill, justinon@usc.edu, and Kyung Woon Jung, kwjung@usc.edu. Department of Chemistry, University of Southern California, 837 Bloom Walk, LHI 132, Los Angeles, CA 90089
Chiral N-heterocyclic carbene (NHC) Pd(II) complex has been successfully prepared. It was found that asymmetric oxidative Heck-type reaction of arylboronic acids with acyclic alkenes took place with high enantioselectivity. For example, phenylboronic acid was allowed to react with trans-2-methyl-2-butenal in the presence of a catalytic amount of the chiral NHC Pd(II) complex under dioxygen atmosphere to afford 2-methylene-3-phenylbutanal as a major product in 95% ee. To the best of our knowledge, this is the first example of asymmetric oxidative Heck-type reaction under dioxygen using chiral NHC Pd(II) complex, yielding high enatiomeric excess.
 

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

Division of Organic Chemistry

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