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Asymmetric indium-mediated Barbier-type allylation reactions with ketones to form homoallylic alcohol products by Terra D. Haddad; Lacie C. Hirayama; Philip Taynton; Bakthan Singaram is a Chemistry article available to read on EtoBox.

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We report a general method for the enantioselective allylation of both aromatic and aliphatic ketones under indium-mediated Barbiertype conditions. Using 2 equiv of a commercially available amino alcohol, either (1S,2R)-(+)-2-amino-1,2-diphenylethanol ((+)-1) or (1R,2S)-(À)-2-amino-1,2-diphenylethanol ((À)-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 a,a,a-trifluoroacetophenone provided 80% enantiomeric excess.

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Author

Terra D. Haddad; Lacie C. Hirayama; Philip Taynton; Bakthan Singaram

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0040-4039)

Published

2008

Language

EN

Field

Chemistry (Physical Sciences)