Asymmetric indium-mediated Barbier-type allylation reactions with ketones to form homoallylic alcohol products

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 (1 S,2 R)-(+)-2-amino-1,2-diphenylethanol ((+)- 1) or (1 R,2 S)-(−)-2-amino-1,2-dipheny...

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Bibliographic Details
Published inTetrahedron letters Vol. 49; no. 3; pp. 508 - 511
Main Authors Haddad, Terra D., Hirayama, Lacie C., Taynton, Philip, Singaram, Bakthan
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.01.2008
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALLYLBORATION
ALDEHYDES
AQUEOUS-MEDIA
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Summary: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 (1 S,2 R)-(+)-2-amino-1,2-diphenylethanol ((+)- 1) or (1 R,2 S)-(−)-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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2007.11.089