Literature DB >> 19507841

Enantio- and diastereoselective intermolecular Stetter reaction of glyoxamide and alkylidene ketoamides.

Qin Liu1, Tomislav Rovis.   

Abstract

A triazolinylidene carbene catalyzed intermolecular Stetter reaction of glyoxamide and alkylidene ketoamides has been developed. 1,4-Dicarbonyl products are afforded in good to excellent yields, enantioselectivities, and diastereoselectivities. Further derivatization of the products affords useful intermediates for organic synthesis.

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Year:  2009        PMID： 19507841      PMCID： PMC2782595          DOI： 10.1021/ol901081a

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  39 in total

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4.  Dynamic kinetic resolution of alpha,beta-unsaturated lactones through asymmetric copper-catalyzed conjugate reduction: application to the total synthesis of eupomatilone-3.

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5.  Catalytic asymmetric synthesis of acyclic arrays by tandem 1,4-addition-aldol reactions.

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8.  Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Authors:  Qin Liu; Stéphane Perreault; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419

9.  Combinatorial Knoevenagel reactions.

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  16 in total

1.  Dynamic kinetic resolution of α-keto esters via asymmetric transfer hydrogenation.

Authors:  Kimberly M Steward; Emily C Gentry; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2012-04-17       Impact factor: 15.419

2.  Catalytic asymmetric intermolecular Stetter reactions of enolizable aldehydes with nitrostyrenes: computational study provides insight into the success of the catalyst.

Authors:  Daniel A DiRocco; Elizabeth L Noey; K N Houk; Tomislav Rovis
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3.  Mechanistic investigation of the enantioselective intramolecular stetter reaction: proton transfer is the first irreversible step.

Authors:  Jennifer L Moore; Anthony P Silvestri; Javier Read de Alaniz; Daniel A DiRocco; Tomislav Rovis
Journal:  Org Lett       Date:  2011-02-28       Impact factor: 6.005

Review 4.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

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Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

5.  Organocatalytic hydroacylation of unactivated alkenes.

Authors:  Daniel A DiRocco; Tomislav Rovis
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6.  Catalytic asymmetric intermolecular Stetter reaction of enals with nitroalkenes: enhancement of catalytic efficiency through bifunctional additives.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-06-16       Impact factor: 15.419

7.  Quantum mechanical investigation of the effect of catalyst fluorination in the intermolecular asymmetric Stetter reaction.

Authors:  Joann M Um; Daniel A DiRocco; Elizabeth L Noey; Tomislav Rovis; K N Houk
Journal:  J Am Chem Soc       Date:  2011-07-06       Impact factor: 15.419

8.  Asymmetric synthesis of α-keto esters via Cu(II)-catalyzed aerobic deacylation of acetoacetate alkylation products: an unusually simple synthetic equivalent to the glyoxylate anion synthon.

Authors:  Kimberly M Steward; Jeffrey S Johnson
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9.  Asymmetric homoenolate additions to acyl phosphonates through rational design of a tailored N-heterocyclic carbene catalyst.

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Review 10.  A continuum of progress: applications of N-hetereocyclic carbene catalysis in total synthesis.

Authors:  Javier Izquierdo; Gerri E Hutson; Daniel T Cohen; Karl A Scheidt
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