Organic Chemistry Portal

Abstracts

Search:

Enantioselective Carbonyl Reverse Prenylation from the Alcohol or Aldehyde Oxidation Level Employing 1,1-Dimethylallene as the Prenyl Donor

Soo Bong Han, In Su Kim, Hoon Han and Michael J. Krische*

*University of Texas at Austin, Department of Chemistry and Biochemistry, Austin, Texas 78712, Email: mkrischemail.utexas.edu

S. B. Han, I. S. Kim, H. Han, M. J. Krische, J. Am. Chem. Soc., 2009, 131, 6916-6917.

DOI: 10.1021/ja902437k (free Supporting Information)


Abstract

Enantioselective transfer hydrogenation of 1,1-dimethylallene in the presence of aldehydes and 2-propanol or primary alcohols without 2-propanol employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, m-nitrobenzoic acid, and (S)-SEGPHOS delivers reverse-prenylation products in very good yields and enantioselectivities.

see article for more examples



Key Words

allylic alcohols, isopropanol


ID: J48-Y2009-1560