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Literature DB >> 22038391

Design, synthesis, and application of tartaric acid derived N-spiro quaternary ammonium salts as chiral phase-transfer catalysts.

Mario Waser¹, Katharina Gratzer, Richard Herchl, Norbert Müller.

Abstract

A novel class of tartaric acid-derived N-spiro quaternary ammonium salts was synthesised starting from known TADDOLs. These compounds were found to catalyse the asymmetric α-alkylation of glycine Schiff bases with high enantioselectivities and in good yields.

Entities: Chemical Disease Gene

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Year: 2011 PMID： 22038391 PMCID： PMC4202190 DOI： 10.1039/c1ob06573d

Source DB: PubMed Journal: Org Biomol Chem ISSN： 1477-0520 Impact factor: 3.876

14 in total

1. Enantio- and diastereoselective catalytic Mannich-type reaction of a glycine schiff base using a chiral two-center phase-transfer catalyst.

Authors: Akihiro Okada; Tomoyuki Shibuguchi; Takashi Ohshima; Hyuma Masu; Kentaro Yamaguchi; Masakatsu Shibasaki
Journal: Angew Chem Int Ed Engl Date: 2005-07-18 Impact factor: 15.336

2. Organocatalytic enantioselective nucleophilic vinylic substitution.

Authors: Thomas B Poulsen; Luca Bernardi; Mark Bell; Karl Anker Jørgensen
Journal: Angew Chem Int Ed Engl Date: 2006-10-06 Impact factor: 15.336

3. Catalytic asymmetric syntheses of isoxazoline-N-oxides under phase-transfer conditions.

Authors: Taichi Kano; Akihiro Yamamoto; Sunhwa Song; Keiji Maruoka
Journal: Chem Commun (Camb) Date: 2011-02-01 Impact factor: 6.222

Review 4. Recent development and application of chiral phase-transfer catalysts.

Authors: Takuya Hashimoto; Keiji Maruoka
Journal: Chem Rev Date: 2007-12 Impact factor: 60.622

5. Catalytic asymmetric 6pi electrocyclization: enantioselective synthesis of functionalized indolines.

Authors: Eleanor E Maciver; Sam Thompson; Martin D Smith
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

6. Organocatalytic asymmetric direct alpha-alkynylation of cyclic beta-ketoesters.

Authors: Thomas B Poulsen; Luca Bernardi; José Aleman; Jacob Overgaard; Karl Anker Jørgensen
Journal: J Am Chem Soc Date: 2007-01-17 Impact factor: 15.419

7. A systematic investigation of quaternary ammonium ions as asymmetric phase-transfer catalysts. Synthesis of catalyst libraries and evaluation of catalyst activity.

Authors: Scott E Denmark; Nathan D Gould; Larry M Wolf
Journal: J Org Chem Date: 2011-05-06 Impact factor: 4.354

8. Highly Enantioselective Asymmetric Darzens Reactions with a Phase Transfer Catalyst.

Authors: Yan Liu; Brian A Provencher; Keith J Bartleson; Li Deng
Journal: Chem Sci Date: 2011-07 Impact factor: 9.825

9. The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral Schiff base esters.

Authors: Martin J O'Donnell
Journal: Acc Chem Res Date: 2004-08 Impact factor: 22.384

10. A remarkable cyclization of TADDOL-bisthioacetate under oxidative conditions.

Authors: Mario Waser; Manuela Haunschmidt; Markus Himmelsbach
Journal: Monatsh Chem Date: 2010-12-01 Impact factor: 1.451

11 in total

1. Investigations Concerning the Syntheses of TADDOL-Derived Secondary Amines and Their Use To Access Novel Chiral Organocatalysts.

Authors: Katharina Gratzer; Mario Waser
Journal: Synthesis (Stuttg) Date: 2012-12 Impact factor: 3.157

2. Asymmetric cyclopropanation of chalcones using chiral phase-transfer catalysts.

Authors: Richard Herchl; Mario Waser
Journal: Tetrahedron Lett Date: 2013-05-15 Impact factor: 2.415

3. Towards an asymmetric organocatalytic α-cyanation of β-ketoesters.

Authors: Raghunath Chowdhury; Johannes Schörgenhumer; Johanna Novacek; Mario Waser
Journal: Tetrahedron Lett Date: 2015-04-01 Impact factor: 2.415

4. Syntheses and Applications of (Thio)Urea-Containing Chiral Quaternary Ammonium Salt Catalysts.

Authors: Johanna Novacek; Mario Waser
Journal: European J Org Chem Date: 2014-02

5. Asymmetric phase-transfer catalysed β-addition of isoxazolidin-5-ones to MBH carbonates.

Authors: Vito Capaccio; Katharina Zielke; Andreas Eitzinger; Antonio Massa; Laura Palombi; Kirill Faust; Mario Waser
Journal: Org Chem Front Date: 2018-10-12 Impact factor: 5.281

6. Application scope and limitations of TADDOL-derived chiral ammonium salt phase-transfer catalysts.

Authors: Guddeangadi N Gururaja; Richard Herchl; Antonia Pichler; Katharina Gratzer; Mario Waser
Journal: Molecules Date: 2013-04-12 Impact factor: 4.411

Review 7. Chiral phase-transfer catalysis in the asymmetric α-heterofunctionalization of prochiral nucleophiles.

Authors: Johannes Schörgenhumer; Maximilian Tiffner; Mario Waser
Journal: Beilstein J Org Chem Date: 2017-08-22 Impact factor: 2.883

8. Synthesis of Both Enantiomers of Chiral Phenylalanine Derivatives Catalyzed by Cinchona Alkaloid Quaternary Ammonium Salts as Asymmetric Phase Transfer Catalysts.

Authors: Lei Jin; Shuai Zhao; Xin Chen
Journal: Molecules Date: 2018-06-12 Impact factor: 4.411

9. Towards Tartaric-Acid-Derived Asymmetric Organocatalysts.

Authors: Katharina Gratzer; Guddeangadi N Gururaja; Mario Waser
Journal: European J Org Chem Date: 2013-06-03

10. 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