Vicinal Amino Alcohols as Organocatalysts in Asymmetric Cross-Aldol Reaction of Ketones:  Application in the Synthesis of Convolutamydine A

Vicinal Amino Alcohols as Organocatalysts in Asymmetric Cross-Aldol Reaction of Ketones:  Application in the Synthesis of Convolutamydine A

Leucinol and valinol have been identified as efficient organocatalysts for the aldol reaction of isatin and its derivatives (as examples of activated, non-enolizable ketones) with acetone. Uncommon mechanistic features were observed and used in the formulation of the transition state of the reaction...

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Bibliographic Details
Published in:Organic letters Vol. 9; no. 26; pp. 5473 - 5476
Main Authors: Malkov, Andrei V, Kabeshov, Mikhail A, Bella, Marco, Kysilka, Ondřej, Malyshev, Denis A, Pluháčková, Kristýna, Kočovský, Pavel
Format: Journal Article
Language:English
Published: United States American Chemical Society 20-12-2007
Online Access:Get full text
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Summary:Leucinol and valinol have been identified as efficient organocatalysts for the aldol reaction of isatin and its derivatives (as examples of activated, non-enolizable ketones) with acetone. Uncommon mechanistic features were observed and used in the formulation of the transition state of the reaction.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol7023983