Asymmetric dihydroxylation of allenes

Graphic We have used asymmetric dihydroxylation (AD) of allenes in order to synthesize chiral α-hydroxy ketones. This methodology has been applied to several aryl-substituted allenes. We have found that electron donating groups on the aromatic ring increase the efficiency of the reaction.

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 17; pp. 3341 - 3343
Main Authors Fleming, Steven A., Carroll, Sean M., Hirschi, Jennifer, Liu, Renmao, Lee Pace, J., Ty Redd, J.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 19.04.2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
α-Hydroxy ketones
α-Hydroxy ketones
OXIDATION
ALCOHOLS
ETHERS
REDUCTION
alpha-hydroxy ketones
EFFICIENT SYNTHESIS
CARBONYL-COMPOUNDS
OLEFINS
ALDEHYDES
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Summary:Graphic We have used asymmetric dihydroxylation (AD) of allenes in order to synthesize chiral α-hydroxy ketones. This methodology has been applied to several aryl-substituted allenes. We have found that electron donating groups on the aromatic ring increase the efficiency of the reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.03.037