Literature DB >> 31830176

Quaternary β2,2-amino acid derivatives by asymmetric addition of isoxazolidin-5-ones to para-quinone methides.

Andreas Eitzinger1, Michael Winter1, Johannes Schörgenhumer1, Mario Waser1.   

Abstract

The highly enantioselective (>99.5% ee) synthesis of a new class of densely functionalized β2,2-amino acid derivatives by reacting isoxazolidin-5-ones with para-quinone methides in the presence of chiral ammonium salt phase-transfer catalysts was developed. The reaction proceeds with exceptionally low catalyst loadings down to 20 ppm on gram scale and the utilization of the primary addition products towards further manipulations was demonstrated for selected examples.

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Year:  2019        PMID： 31830176      PMCID： PMC7082149          DOI： 10.1039/c9cc09239k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  40 in total

Review 1.  Recent developments in the catalytic asymmetric synthesis of alpha- and beta-amino acids.

Authors:  Jun-An Ma
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2.  Compounds binding to the S2-S3 pockets of thrombin.

Authors:  Mikael Nilsson; Markku Hämäläinen; Maria Ivarsson; Johan Gottfries; Yafeng Xue; Sebastian Hansson; Roland Isaksson; Tomas Fex
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3.  Organocatalysed decarboxylative protonation process from Meldrum's acid: enantioselective synthesis of isoxazolidinones.

Authors:  Tony Tite; Mohamad Sabbah; Vincent Levacher; Jean-François Brière
Journal:  Chem Commun (Camb)       Date:  2013-12-21       Impact factor: 6.222

4.  Amide-Phosphonium Salt as Bifunctional Phase Transfer Catalyst for Asymmetric 1,6-Addition of Malonate Esters to para-Quinone Methides.

Authors:  Luo Ge; Xuehe Lu; Cang Cheng; Jie Chen; Weiguo Cao; Xiaoyu Wu; Gang Zhao
Journal:  J Org Chem       Date:  2016-09-26       Impact factor: 4.354

5.  Traceless Electrophilic Amination for the Synthesis of Unprotected Cyclic β-Amino Acids.

Authors:  Jin-Sheng Yu; Miguel Espinosa; Hidetoshi Noda; Masakatsu Shibasaki
Journal:  J Am Chem Soc       Date:  2019-06-21       Impact factor: 15.419

6.  Palladium-Catalyzed Asymmetric Allylic Alkylation of 4-Substituted Isoxazolidin-5-ones: Straightforward Access to β2,2 -Amino Acids.

Authors:  Marllon Nascimento de Oliveira; Stellios Arseniyadis; Janine Cossy
Journal:  Chemistry       Date:  2018-03-13       Impact factor: 5.236

7.  Exploiting β-Amino Acid Enolates in Direct Catalytic Diastereo- and Enantioselective C-C Bond-Forming Reactions.

Authors:  Jin-Sheng Yu; Hidetoshi Noda; Masakatsu Shibasaki
Journal:  Chemistry       Date:  2018-10-08       Impact factor: 5.236

8.  Enantioselective Michael addition of alpha-substituted cyanoacetates to vinyl ketones catalyzed by bifunctional organocatalysts.

Authors:  Tian-Yu Liu; Rui Li; Qian Chai; Jun Long; Bang-Jing Li; Yong Wu; Li-Sheng Ding; Ying-Chun Chen
Journal:  Chemistry       Date:  2007       Impact factor: 5.236

9.  Traceless preparation of C-terminal α-ketoacids for chemical protein synthesis by α-ketoacid-hydroxylamine ligation: synthesis of SUMO2/3.

Authors:  Thomas G Wucherpfennig; Vijaya R Pattabiraman; Felix R P Limberg; Javier Ruiz-Rodríguez; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-22       Impact factor: 15.336

10.  The domestication of ortho-quinone methides.

Authors:  Wen-Ju Bai; Jonathan G David; Zhen-Gao Feng; Marisa G Weaver; Kun-Liang Wu; Thomas R R Pettus
Journal:  Acc Chem Res       Date:  2014-12-03       Impact factor: 22.384
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  8 in total

1.  Enantioselective catalytic synthesis of α-aryl-α-SCF3-β2,2-amino acids.

Authors:  Andreas Eitzinger; Jean-François Brière; Dominique Cahard; Mario Waser
Journal:  Org Biomol Chem       Date:  2020-01-22       Impact factor: 3.876

2.  CF3-Containing para-Quinone Methides for Organic Synthesis.

Authors:  Michael Winter; Roman Schütz; Andreas Eitzinger; Armin R Ofial; Mario Waser
Journal:  European J Org Chem       Date:  2020-03-06

3.  Enantioselective organocatalytic syntheses of α-selenated α- and β-amino acid derivatives.

Authors:  Victoria Haider; Paul Zebrowski; Jessica Michalke; Uwe Monkowius; Mario Waser
Journal:  Org Biomol Chem       Date:  2022-01-26       Impact factor: 3.890

4.  Enantioselective Catalytic Synthesis of α-Halogenated α-Aryl-β2,2-amino Acid Derivatives.

Authors:  Paul Zebrowski; Isabella Eder; Andreas Eitzinger; Sharath Chandra Mallojjala; Mario Waser
Journal:  ACS Org Inorg Au       Date:  2021-09-24

5.  Synthesis of β2,2-Amino Acids by Stereoselective Alkylation of Isoserine Derivatives Followed by Nucleophilic Ring Opening of Quaternary Sulfamidates.

Authors:  Pablo Tovillas; Claudio D Navo; Paula Oroz; Alberto Avenoza; Francisco Corzana; María M Zurbano; Gonzalo Jiménez-Osés; Jesús H Busto; Jesús M Peregrina
Journal:  J Org Chem       Date:  2022-06-22       Impact factor: 4.198

6.  Electrophilic Reactivities of Vinyl p-Quinone Methides.

Authors:  Andreas Eitzinger; Robert J Mayer; Nathalie Hampel; Peter Mayer; Mario Waser; Armin R Ofial
Journal:  Org Lett       Date:  2020-03-02       Impact factor: 6.005

7.  Ammonium Salt-Catalyzed Ring-Opening of Aryl-Aziridines with β-Keto Esters.

Authors:  Victoria Haider; Viktoria Kreuzer; Maximilian Tiffner; Bernhard Spingler; Mario Waser
Journal:  European J Org Chem       Date:  2020-07-15

8.  Enantioselective Synthesis of Acyclic Orthogonally Functionalized Compounds Bearing a Quaternary Stereocenter Using Chiral Ammonium Salt Catalysis.

Authors:  Katharina Röser; Bettina Berger; Michael Widhalm; Mario Waser
Journal:  ChemistryOpen       Date:  2021-08       Impact factor: 2.630
  8 in total

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