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)
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.
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