Literature DB >> 16235956

Bifunctional AgOAc-catalyzed asymmetric [3 + 2] cycloaddition of azomethine ylides.

Wei Zeng1, Yong-Gui Zhou.   

Abstract

[reaction: see text] A bifunctional AgOAc-catalyzed asymmetric cycloaddition of azomethine ylides with electronic-deficient alkenes was developed using ferrocenyloxazoline-derived N,P ligands. The reactive metal-bound azomethine ylide dipole is formed by the deprotonation with acetate, and extra base is not necessary. The reactions proceed with high enantioselectivity. This method provides an efficient and convenient route to optically active pyrrolidine derivatives.

Entities:  

Year:  2005        PMID: 16235956     DOI: 10.1021/ol0520370

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  5 in total

1.  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

2.  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

3.  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

4.  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

5.  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

  5 in total

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