Literature DB >> 18841892

Highly diastereoselective switchable enantioselective Mannich reaction of glycine derivatives with imines.

Xiao-Xia Yan1, Qian Peng, Qing Li, Kai Zhang, Jun Yao, Xue-Long Hou, Yun-Dong Wu.   

Abstract

Tuning of diastereoselectivity was realized in the Mannich reaction of glycine derivatives with aromatic and aliphatic N-Ts imines using CuClO4-FcPHOX ligand 4b and 4f having an MeO group at the 4-position and F atom at the 3,5-position of the phenyl ring on the P-atom respectively as catalyst, providing either anti- or syn-alpha,beta-diamino acid derivatives in high yields and in high diastereo- and enantioselectivities.

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Year:  2008        PMID: 18841892     DOI: 10.1021/ja804527r

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


  13 in total

1.  Stereodivergent Allylic Substitutions with Aryl Acetic Acid Esters by Synergistic Iridium and Lewis Base Catalysis.

Authors:  Xingyu Jiang; Jason J Beiger; John F Hartwig
Journal:  J Am Chem Soc       Date:  2016-12-22       Impact factor: 15.419

2.  Cyclopropenimine-catalyzed enantioselective Mannich reactions of tert-butyl glycinates with N-Boc-imines.

Authors:  Jeffrey S Bandar; Tristan H Lambert
Journal:  J Am Chem Soc       Date:  2013-08-01       Impact factor: 15.419

3.  Catalytic Asymmetric Mannich Reaction of α-Fluoronitriles with Ketimines: Enantioselective and Diastereodivergent Construction of Vicinal Tetrasubstituted Stereocenters.

Authors:  Ransheng Ding; Zeus A De Los Santos; Christian Wolf
Journal:  ACS Catal       Date:  2019-02-06       Impact factor: 13.084

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.  Copper-catalysed enantioselective stereodivergent synthesis of amino alcohols.

Authors:  Shi-Liang Shi; Zackary L Wong; Stephen L Buchwald
Journal:  Nature       Date:  2016-03-28       Impact factor: 49.962

6.  Complete diastereodivergence in asymmetric 1,6-addition reactions enabled by minimal modification of a chiral catalyst.

Authors:  Daisuke Uraguchi; Ken Yoshioka; Takashi Ooi
Journal:  Nat Commun       Date:  2017-03-20       Impact factor: 14.919

7.  Stereodivergent, Diels-Alder-initiated organocascades employing α,β-unsaturated acylammonium salts: scope, mechanism, and application.

Authors:  Mikail E Abbasov; Brandi M Hudson; Dean J Tantillo; Daniel Romo
Journal:  Chem Sci       Date:  2016-10-21       Impact factor: 9.825

8.  Pd-catalyzed asymmetric allylic alkylations via C-H activation of N-allyl imines with glycinates.

Authors:  Barry M Trost; Xiaoxun Li
Journal:  Chem Sci       Date:  2017-08-15       Impact factor: 9.825

9.  Organocatalytic and enantioselective Michael reaction between α-nitroesters and nitroalkenes. Syn/anti-selectivity control using catalysts with the same absolute backbone chirality.

Authors:  Jose I Martínez; Uxue Uria; Maria Muñiz; Efraím Reyes; Luisa Carrillo; Jose L Vicario
Journal:  Beilstein J Org Chem       Date:  2015-12-14       Impact factor: 2.883

10.  Diastereo- and enantioselective additions of α-nitro esters to imines for anti-α,β-diamino acid synthesis with α-alkyl-substitution.

Authors:  Daniel J Sprague; Anand Singh; Jeffrey N Johnston
Journal:  Chem Sci       Date:  2018-01-31       Impact factor: 9.825

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