Organic Chemistry Portal



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:

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

DOI: 10.1021/ja902437k


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

homoallylic alcohols, isopropanol

ID: J48-Y2009-1560