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A Direct Catalytic Asymmetric Mannich-type Reaction to syn-Amino Alcohols
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Section:Abstract
The Mannich reaction is one of the most widely utilized chemical transformations for the construction of nitrogen-containing compounds. With the increasing occurrence of nitrogen in drugs and natural products, highly asymmetric variants of the Mannich reaction are desirable. In this communication, we report the application of our dinuclear zinc catalyst to a highly asymmetric Mannich-type reaction to generate syn 1,2-amino alcohols.
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This article has been cited by 55 ACS Journal articles (5 most recent appear below).
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Enantioselective Synthesis of Optically Pure β-Amino Ketones and γ-Aryl Amines by Rh-Catalyzed Asymmetric Hydrogenation
Huiling Geng, Kexuan Huang, Tian Sun, Wei Li, Xiaowei Zhang, Le Zhou, Wenjun Wu, and Xumu ZhangThe Journal of Organic Chemistry2011 76 (1), 332-334Enantioselective Synthesis of Optically Pure β-Amino Ketones and γ-Aryl Amines by Rh-Catalyzed Asymmetric Hydrogenation
Huiling Geng, Kexuan Huang, Tian Sun, Wei Li, Xiaowei Zhang, Le Zhou, Wenjun Wu, and Xumu ZhangThe Journal of Organic Chemistry2011 76 (1), 332-334A series of optically pure β-amino ketones have been synthesized in high enantioselectivities (ee > 99%) by Rh-DuanPhos-catalyzed asymmetric hydrogenation of readily prepared β-keto enamides. Further reduction of these β-amino ketones with hydrogen and Pd/...
Development of Bifunctional Aza-Bis(oxazoline) Copper Catalysts for Enantioselective Henry Reaction
Kai Lang, Jongwoo Park, and Sukwon HongThe Journal of Organic Chemistry2010 75 (19), 6424-6435Development of Bifunctional Aza-Bis(oxazoline) Copper Catalysts for Enantioselective Henry Reaction
Kai Lang, Jongwoo Park, and Sukwon HongThe Journal of Organic Chemistry2010 75 (19), 6424-6435Base-functionalized aza-bis(oxazoline) ligands were prepared to explore the concept of dual activation through the Lewis acid and a tethered tertiary amine base. The catalytic activity of the Cu complex was evaluated for the asymmetric Henry reaction. ...
Enantioselective ProPhenol-Catalyzed Addition of 1,3-Diynes to Aldehydes to Generate Synthetically Versatile Building Blocks and Diyne Natural Products
Barry M. Trost, Vincent S. Chan and Daisuke YamamotoJournal of the American Chemical Society2010 132 (14), 5186-5192Enantioselective ProPhenol-Catalyzed Addition of 1,3-Diynes to Aldehydes to Generate Synthetically Versatile Building Blocks and Diyne Natural Products
Barry M. Trost, Vincent S. Chan and Daisuke YamamotoJournal of the American Chemical Society2010 132 (14), 5186-5192A highly enantioselective method for the catalytic addition of terminal 1,3-diynes to aldehydes was developed using our dinuclear zinc ProPhenol (1) system. Furthermore, triphenylphosphine oxide was found to interact synergistically with the catalyst to ...
Three-Component Synthesis of α-Branched Amines under Barbier-like Conditions
Erwan Le Gall, Caroline Haurena, Stéphane Sengmany, Thierry Martens and Michel TroupelThe Journal of Organic Chemistry2009 74 (20), 7970-7973Three-Component Synthesis of α-Branched Amines under Barbier-like Conditions
Erwan Le Gall, Caroline Haurena, Stéphane Sengmany, Thierry Martens and Michel TroupelThe Journal of Organic Chemistry2009 74 (20), 7970-7973An array of α-branched amines has been prepared by using an expedient three-component Mannich-type reaction among organic halides, aldehyde derivatives, and amines. The experimental procedure, which is characterized by its simplicity, employs zinc dust ...
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History
- Published In Issue January 15, 2003
- Received October 2, 2002
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