Literature DB >> 18646755

Chiral ammonium betaines: a bifunctional organic base catalyst for asymmetric Mannich-type reaction of alpha-nitrocarboxylates.

Daisuke Uraguchi1, Kyohei Koshimoto, Takashi Ooi.   

Abstract

A chiral ammonium betaine, an intramolecular ion-pairing quaternary ammonium aryloxide 3, has been designed and its vast potential as an enantioselective organic base catalyst has been successfully demonstrated in the highly enantioselective direct Mannich-type reaction of alpha-substituted alpha-nitrocarboxylates 2 with various N-Boc imines 1. The present study provides a conceptually new approach toward the design of bifunctional, chiral quaternary ammonium salts and their utilizations as a homogeneous organic molecular catalyst.

Entities:  

Year:  2008        PMID： 18646755     DOI： 10.1021/ja8041004

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


  12 in total

1.  Asymmetric catalytic N-phosphonyl imine chemistry: the use of primary free amino acids and Et2AlCN for asymmetric catalytic Strecker reaction.

Authors:  Parminder Kaur; Suresh Pindi; Walter Wever; Trideep Rajale; Guigen Li
Journal:  J Org Chem       Date:  2010-08-06       Impact factor: 4.354

2.  Enantioselective Addition of Bromonitromethane to Aliphatic N-Boc Aldimines Using a Homogeneous Bifunctional Chiral Organocatalyst.

Authors:  Kenneth E Schwieter; Jeffrey N Johnston
Journal:  ACS Catal       Date:  2015       Impact factor: 13.084

3.  Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.

Authors:  Saki Ichikawa; Xi-Jie Dai; Stephen L Buchwald
Journal:  Org Lett       Date:  2019-05-17       Impact factor: 6.005

4.  DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters.

Authors:  Thomas J Struble; Ivor Smajlagic; Hayden Foy; Travis Dudding; Jeffrey N Johnston
Journal:  J Org Chem       Date:  2021-10-20       Impact factor: 4.354

5.  Cinchonium Betaines as Efficient Catalysts for Asymmetric Proton Transfer Catalysis: The Development of a Practical Enantioselective Isomerization of Trifluoromethyl Imines.

Authors:  Xiao Zhou; Yongwei Wu; Li Deng
Journal:  J Am Chem Soc       Date:  2016-09-09       Impact factor: 15.419

6.  Enantioselective Synthesis of anti-1,2-Diamines by Cu-Catalyzed Reductive Couplings of Azadienes with Aldimines and Ketimines.

Authors:  Xinxin Shao; Kangnan Li; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2018-05-30       Impact factor: 15.419

7.  Enantioselective Addition of α-Nitroesters to Alkynes.

Authors:  Ryan T Davison; Patrick D Parker; Xintong Hou; Crystal P Chung; Sara A Augustine; Vy M Dong
Journal:  Angew Chem Int Ed Engl       Date:  2021-01-07       Impact factor: 15.336

8.  A Diastereodivergent and Enantioselective Approach to syn- and anti-Diamines: Development of 2-Azatrienes for Cu-Catalyzed Reductive Couplings with Imines That Furnish Allylic Amines.

Authors:  Pengfei Zhou; Xinxin Shao; Steven J Malcolmson
Journal:  J Am Chem Soc       Date:  2021-08-23       Impact factor: 16.383

9.  Vicinal diamination of alkenes under Rh-catalysis.

Authors:  David E Olson; Justin Y Su; D Allen Roberts; J Du Bois
Journal:  J Am Chem Soc       Date:  2014-09-18       Impact factor: 15.419

10.  Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles.

Authors:  Masahiro Torii; Kohsuke Kato; Daisuke Uraguchi; Takashi Ooi
Journal:  Beilstein J Org Chem       Date:  2016-09-28       Impact factor: 2.883
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