Literature DB >> 12418889

Highly enantioselective Ag(i)-catalyzed [3 + 2] cycloaddition of azomethine ylides.

James M Longmire1, Bin Wang, Xumu Zhang.   

Abstract

A highly reactive Ag(I)-catalyzed [3 + 2] cycloaddition of azomethine ylides is founded using AgOAc as the catalytic precursor and phosphines as ligands. Using a new bis-ferrocenyl amide phosphine (FAP) as the ligand, we found that high enantioselectivities (up to 97% ee) have been achieved in the [3 + 2] cycloaddition of azomethine ylides. Up to four stereogenic centers can be established in this multicomponent coupling reaction from readily available materials such as aldehydes, aminoesters, and dipolarophiles.

Entities:  

Mesh:

Substances:

Year:  2002        PMID: 12418889     DOI: 10.1021/ja025969x

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


  13 in total

1.  Enantioselective construction of pyrrolidines by palladium-catalyzed asymmetric [3 + 2] cycloaddition of trimethylenemethane with imines.

Authors:  Barry M Trost; Steven M Silverman
Journal:  J Am Chem Soc       Date:  2012-03-02       Impact factor: 15.419

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.  Development of a 2-aza-Cope-[3 + 2] dipolar cycloaddition strategy for the synthesis of quaternary proline scaffolds.

Authors:  Michael P McCormack; Tamila Shalumova; Joseph M Tanski; Stephen P Waters
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

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.  1,2:5,6-Di-O-isopropyl-idene-α-d-3-glucofuranosyl (R(p))-2-(diphenyl-phosphino)ferrocene-1-carboxyl-ate.

Authors:  Petr Stěpnička; Martin Lamač; Ivana Císařová
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-30

7.  Solventless lactam synthesis by intramolecular cyclizations of alpha-iminoester derivatives under microwave irradiation.

Authors:  Fatima-Zohra Zradni; Jack Hamelin; Aicha Derdour
Journal:  Molecules       Date:  2007-03-12       Impact factor: 4.411

8.  Stereoselective Synthesis of Quaternary Proline Analogues.

Authors:  M Isabel Calaza; Carlos Cativiela
Journal:  European J Org Chem       Date:  2008

9.  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

10.  Catalytic enantioselective 1,3-dipolar cycloadditions of azomethine ylides for biology-oriented synthesis.

Authors:  Rishikesh Narayan; Marco Potowski; Zhi-Jun Jia; Andrey P Antonchick; Herbert Waldmann
Journal:  Acc Chem Res       Date:  2014-03-22       Impact factor: 22.384

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.