Asymmetric indium-mediated Barbier-type allylation reactions with ketones to form homoallylic alcohol products |
| |
Authors: | Terra D Haddad |
| |
Institution: | Department of Chemistry and Biochemistry, University of California at Santa Cruz, 1156 High Street, Santa Cruz, CA 95064, United States |
| |
Abstract: | We report a general method for the enantioselective allylation of both aromatic and aliphatic ketones under indium-mediated Barbier-type conditions. Using 2 equiv of a commercially available amino alcohol, either (1S,2R)-(+)-2-amino-1,2-diphenylethanol ((+)-1) or (1R,2S)-(−)-2-amino-1,2-diphenylethanol ((−)-1) as the chiral auxiliary, good yields and enantioselectivities were achieved. To our knowledge, the enantioselectivities reported herein are the highest obtained for the indium-mediated allylations of ketones, specifically the homoallylic alcohol product obtained from the addition to α,α,α-trifluoroacetophenone provided 80% enantiomeric excess. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|