Literature DB >> 19035782

Highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides catalyzed by copper(I)/TF-BiphamPhos complexes.

Chun-Jiang Wang1, Gang Liang, Zhi-Yong Xue, Feng Gao.   

Abstract

A new and highly efficient Cu(I)/TF-BiphamPhos catalytic system exhibited excellent reactivity, enantio-/diastereoselectivity, and structural scope in asymmetric 1,3-dipolar cycloaddition of azomethine ylides with 0.1-3 mol % of catalyst loading. The present methodology is the best result for asymmetric cycloaddition of azomethine ylides, especially derived from amino esters other than glycinate in terms of reactivity and enantioselectivity.

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Year:  2008        PMID： 19035782     DOI： 10.1021/ja807669q

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


  10 in total

1.  Highly enantioselective synthesis and cellular evaluation of spirooxindoles inspired by natural products.

Authors:  Andrey P Antonchick; Claas Gerding-Reimers; Mario Catarinella; Markus Schürmann; Hans Preut; Slava Ziegler; Daniel Rauh; Herbert Waldmann
Journal:  Nat Chem       Date:  2010-07-11       Impact factor: 24.427

2.  Gold(I)-catalyzed diastereo- and enantioselective 1,3-dipolar cycloaddition and Mannich reactions of azlactones.

Authors:  Asa D Melhado; Giovanni W Amarante; Z Jane Wang; Marco Luparia; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-02-22       Impact factor: 15.419

3.  Phosphoramidite gold(I)-catalyzed diastereo- and enantioselective synthesis of 3,4-substituted pyrrolidines.

Authors:  Ana Z González; Diego Benitez; Ekaterina Tkatchouk; William A Goddard; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-03-23       Impact factor: 15.419

4.  Design and Synthesis of Pyrrolidine-based Fragments That Sample Three-dimensional Molecular Space.

Authors:  Philip Garner; Philip B Cox; Upendra Rathnayake; Nicholas Holloran; Paul Erdman
Journal:  ACS Med Chem Lett       Date:  2019-04-12       Impact factor: 4.345

5.  Anefficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloadditions.

Authors:  Salvatore Filippone; Enrique E Maroto; Ángel Martín-Domenech; Margarita Suarez; Nazario Martín
Journal:  Nat Chem       Date:  2009-10       Impact factor: 24.427

6.  Practical asymmetric amine nucleophilic approach for the modular construction of protected α-quaternary amino acids.

Authors:  Teng Liu; Shaofei Ni; Wusheng Guo
Journal:  Chem Sci       Date:  2022-06-05       Impact factor: 9.969

7.  Catalytic Asymmetric Synthesis of Highly Substituted Pyrrolizidines.

Authors:  Andrew D Lim; Julian A Codelli; Sarah E Reisman
Journal:  Chem Sci       Date:  2012-11-13       Impact factor: 9.825

8.  Development of chiral metal amides as highly reactive catalysts for asymmetric [3 + 2] cycloadditions.

Authors:  Yasuhiro Yamashita; Susumu Yoshimoto; Mark J Dutton; Shū Kobayashi
Journal:  Beilstein J Org Chem       Date:  2016-07-13       Impact factor: 2.883

9.  Enantiomerically Enriched 1,2-P,N-Bidentate Ferrocenyl Ligands for 1,3-Dipolar Cycloaddition and Transfer Hydrogenation Reactions.

Authors:  Irina A Utepova; Polina O Serebrennikova; Marina S Streltsova; Alexandra A Musikhina; Tatiana G Fedorchenko; Oleg N Chupakhin; Andrey P Antonchick
Journal:  Molecules       Date:  2018-05-30       Impact factor: 4.411

10.  Catalytic asymmetric synthesis of enantioenriched α-deuterated pyrrolidine derivatives.

Authors:  Xin Chang; Xiang Cheng; Chun-Jiang Wang
Journal:  Chem Sci       Date:  2022-03-17       Impact factor: 9.825
  10 in total

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