Literature DB >> 24730733

Dynamic kinetic asymmetric [3 + 2] annulation reactions of aminocyclopropanes.

Florian de Nanteuil1, Eloisa Serrano, Daniele Perrotta, Jerome Waser.   

Abstract

We report the first example of a dynamic kinetic asymmetric [3 + 2] annulation reaction of aminocyclopropanes with both enol ethers and aldehydes. Using a Cu catalyst and a commercially available bisoxazoline ligand, cyclopentyl- and tetrahydrofurylamines were obtained in 69-99% yield and up to a 98:2 enantiomeric ratio using the same reaction conditions. The method gives access to important enantio-enriched nitrogen building blocks for the synthesis of bioactive compounds.

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Year:  2014        PMID: 24730733     DOI: 10.1021/ja5024578

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


  17 in total

1.  Further Developments and Applications of Oxazoline-Containing Ligands in Asymmetric Catalysis.

Authors:  Robert Connon; Brendan Roche; Balaji V Rokade; Patrick J Guiry
Journal:  Chem Rev       Date:  2021-05-21       Impact factor: 60.622

2.  Advances in Stereoconvergent Catalysis from 2005 to 2015: Transition-Metal-Mediated Stereoablative Reactions, Dynamic Kinetic Resolutions, and Dynamic Kinetic Asymmetric Transformations.

Authors:  Vikram Bhat; Eric R Welin; Xuelei Guo; Brian M Stoltz
Journal:  Chem Rev       Date:  2017-02-06       Impact factor: 60.622

3.  Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers.

Authors:  Xinxin Shao; Steven J Malcolmson
Journal:  Org Lett       Date:  2019-08-29       Impact factor: 6.005

4.  Radical differentiation of two ester groups in unsymmetrical diazomalonates for highly asymmetric olefin cyclopropanation.

Authors:  Jingyi Wang; Jingjing Xie; Wan-Chen Cindy Lee; Duo-Sheng Wang; X Peter Zhang
Journal:  Chem Catal       Date:  2021-12-29

5.  One-Pot Catalytic Asymmetric Synthesis of Tetrahydrocarbazoles.

Authors:  Qiong-Jie Liu; Wen-Guang Yan; Lijia Wang; X Peter Zhang; Yong Tang
Journal:  Org Lett       Date:  2015-08-07       Impact factor: 6.005

6.  Selective Approaches to α- and β-Arylated Vinyl Ethers.

Authors:  Anna Domzalska-Pieczykolan; Ignacio Funes-Ardoiz; Bartłomiej Furman; Carsten Bolm
Journal:  Angew Chem Int Ed Engl       Date:  2021-11-23       Impact factor: 16.823

7.  Synergistic chiral iminium and palladium catalysis: Highly regio- and enantioselective [3 + 2] annulation reaction of 2-vinylcyclopropanes with enals.

Authors:  Haipan Zhu; Peile Du; Jianjun Li; Ziyang Liao; Guohua Liu; Hao Li; Wei Wang
Journal:  Beilstein J Org Chem       Date:  2016-06-29       Impact factor: 2.883

8.  Dearomatization of electron poor six-membered N-heterocycles through [3 + 2] annulation with aminocyclopropanes.

Authors:  Johannes Preindl; Shyamal Chakrabarty; Jérôme Waser
Journal:  Chem Sci       Date:  2017-08-25       Impact factor: 9.825

9.  Catalytic (3 + 2) annulation of donor-acceptor aminocyclopropane monoesters and indoles.

Authors:  Vincent Pirenne; Emma G L Robert; Jerome Waser
Journal:  Chem Sci       Date:  2021-05-05       Impact factor: 9.825

10.  Diastereo- and enantioselective [3 + 3] cycloaddition of spirocyclopropyl oxindoles using both aldonitrones and ketonitrones.

Authors:  Peng-Wei Xu; Jia-Kuan Liu; Lan Shen; Zhong-Yan Cao; Xiao-Li Zhao; Jun Yan; Jian Zhou
Journal:  Nat Commun       Date:  2017-11-20       Impact factor: 14.919

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