Literature DB >> 28252953

Synthesis of Complex Tertiary Glycolates by Enantioconvergent Arylation of Stereochemically Labile α-Keto Esters.

Samuel L Bartlett1, Kimberly M Keiter1, Jeffrey S Johnson1.   

Abstract

Enantioconvergent arylation reactions of boronic acids and racemic β-stereogenic α-keto esters have been developed. The reactions are catalyzed by a chiral (diene)Rh(I) complex and provide a wide array of β-stereogenic tertiary aryl glycolate derivatives with high levels of diastereo- and enantioselectivity. Racemization studies employing a series of sterically differentiated tertiary amines suggest that the steric nature of the amine base additive exerts a significant influence on the rate of substrate racemization.

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Year:  2017        PMID： 28252953      PMCID： PMC5352479          DOI： 10.1021/jacs.7b00943

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  32 in total

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Journal:  J Am Chem Soc       Date:  2012-04-17       Impact factor: 15.419

2.  Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins.

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3.  Highly diastereo- and enantioselective organocatalytic addition of acetone to beta-substituted alpha-ketoesters via dynamic kinetic resolution.

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Journal:  Org Biomol Chem       Date:  2009-04-16       Impact factor: 3.876

4.  Enantioselective rhodium-catalyzed addition of arylboronic acids to alpha-ketoesters.

Authors:  Hai-Feng Duan; Jian-Hua Xie; Xiang-Chen Qiao; Li-Xin Wang; Qi-Lin Zhou
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

5.  Catalytic dynamic kinetic resolutions with N-heterocyclic carbenes: asymmetric synthesis of highly substituted β-lactones.

Authors:  Daniel T Cohen; Chad C Eichman; Eric M Phillips; Emily R Zarefsky; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-14       Impact factor: 15.336

6.  Enantioselective monoreduction of 2-alkyl-1,3-diketones mediated by chiral ruthenium catalysts. dynamic kinetic resolution.

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Authors:  Jelena Stoimenovski; Ekaterina I Izgorodina; Douglas R MacFarlane
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8.  A tandem organocatalytic α-chlorination-aldol reaction that proceeds with dynamic kinetic resolution: a powerful tool for carbohydrate synthesis.

Authors:  Milan Bergeron-Brlek; Timothy Teoh; Robert Britton
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9.  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

10.  Dynamic kinetic asymmetric cross-benzoin additions of β-stereogenic α-keto esters.

Authors:  C Guy Goodman; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2014-10-09       Impact factor: 15.419
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  8 in total

1.  Synthesis of Complex Glycolates by Enantioconvergent Addition Reactions.

Authors:  Samuel L Bartlett; Jeffrey S Johnson
Journal:  Acc Chem Res       Date:  2017-08-17       Impact factor: 22.384

2.  Direct Zinc(II)-Catalyzed Enantioconvergent Additions of Terminal Alkynes to α-Keto Esters.

Authors:  Blane P Zavesky; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2017-06-20       Impact factor: 15.336

3.  Stereoconvergent Conjugate Addition of Arylboronic Acids to α-Angelica Lactone Derivatives: Synthesis of Stereochemically Complex γ-Butyrolactones.

Authors:  Jessica A Griswold; Jeffrey S Johnson
Journal:  ACS Catal       Date:  2019-11-19       Impact factor: 13.084

4.  Palladium-Catalyzed β-Arylation of α-Keto Esters.

Authors:  Blane P Zavesky; Samuel L Bartlett; Jeffrey S Johnson
Journal:  Org Lett       Date:  2017-04-11       Impact factor: 6.005

5.  Ru-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes via P-Chiral Monophosphorous Ligands.

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Journal:  Molecules       Date:  2022-06-17       Impact factor: 4.927

6.  C(sp3)-Arylation by Conformationally Accelerated Intramolecular Nucleophilic Aromatic Substitution (SNAr).

Authors:  Steven M Wales; Rakesh K Saunthwal; Jonathan Clayden
Journal:  Acc Chem Res       Date:  2022-05-27       Impact factor: 24.466

7.  Stereodivergent Nucleophilic Additions to Racemic β-Oxo Acid Derivatives: Fast Addition Outcompetes Stereoconvergence in the Archetypal Configurationally Unstable Electrophile.

Authors:  Pedro De Jesús Cruz; Evan T Crawford; Shubin Liu; Jeffrey S Johnson
Journal:  J Am Chem Soc       Date:  2021-09-27       Impact factor: 16.383

8.  Access to enantioenriched compounds bearing challenging tetrasubstituted stereocenters via kinetic resolution of auxiliary adjacent alcohols.

Authors:  Shengtong Niu; Hao Zhang; Weici Xu; Prasanta Ray Bagdi; Guoxiang Zhang; Jinggong Liu; Shuang Yang; Xinqiang Fang
Journal:  Nat Commun       Date:  2021-06-18       Impact factor: 14.919
  8 in total

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