Nickel-catalyzed allene−aldehyde and alkene−aldehyde coupling reactions

ORGN 26

Szesze Ng, ngcc@mit.edu and Timothy F. Jamison, tfj@mit.edu. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Ave, Building 18-223, Cambridge, MA 02139
Two approaches to prepare allylic alcohols are presented. A nickel-catalyzed coupling of enantiomerically enriched 1,3-disubstituted allenes, aromatic aldehydes, and organosilanes provides Z-allylic alcohols in high enantiomeric excess. Allylic alcohols can also be prepared in good yield from a nickel-catalyzed coupling of unactivated alkenes, aldehydes, and silyl triflates. By tuning the nickel catalyst with an appropriate supporting ligand, either an allylic or a homoallylic alcohol can be obtained from the nickel-catalyzed alkene−aldehyde coupling.

 

Metal-Mediated Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, August 19, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

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