Literature DB >> 19527029

Brønsted base/Lewis acid cooperative catalysis in the enantioselective Conia-ene reaction.

Ting Yang1, Alessandro Ferrali, Filippo Sladojevich, Leonie Campbell, Darren J Dixon.   

Abstract

A mutually compatible and cooperative combination of copper(I) triflate and bifunctional 9-amino-9-deoxyepicinchona-derived urea compounds for the enantioselective Conia-ene cyclization of alkyne-tethered beta-ketoester substrates is reported. The reaction is efficient, broad in scope, and easy to perform and allows access to chiral methylenecyclopentane products with high enantiocontrol. The transformation illustrates the concept of combining inactive precatalysts with inactive transition-metal-ion complexes in situ to reversibly create a catalytically active combination of the two.

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Year:  2009        PMID： 19527029     DOI： 10.1021/ja9004859

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


  10 in total

1.  Cooperative N-heterocyclic carbene/Lewis acid catalysis for highly stereoselective annulation reactions with homoenolates.

Authors:  Benoit Cardinal-David; Dustin E A Raup; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2010-04-21       Impact factor: 15.419

2.  Enantioselective Conia-Ene-Type Cyclizations of Alkynyl Ketones through Cooperative Action of B(C6F5)3, N-Alkylamine and a Zn-Based Catalyst.

Authors:  Min Cao; Ahmet Yesilcimen; Masayuki Wasa
Journal:  J Am Chem Soc       Date:  2019-02-27       Impact factor: 15.419

3.  Brønsted Acid/Lewis Acid Cooperatively Catalyzed Addition of Diazoester to 2H-chromene Acetals.

Authors:  Yi Luan; Yue Qi; Hongyi Gao; Qianqian Ma; Scott E Schaus
Journal:  European J Org Chem       Date:  2014-11-01

Review 4.  Recent Advances in Catalytic Alkyne Transformation via Copper Carbene Intermediates.

Authors:  Kuiyong Dong; Mengting Liu; Xinfang Xu
Journal:  Molecules       Date:  2022-05-11       Impact factor: 4.927

5.  A Ruthenium-Catalyzed Coupling of Alkynes with 1,3-Diketones.

Authors:  Megan K Pennington-Boggio; Brian L Conley; Travis J Williams
Journal:  J Organomet Chem       Date:  2012-05-25       Impact factor: 2.369

6.  Catalytic asymmetric Nakamura reaction by gold(I)/chiral N,N'-dioxide-indium(III) or nickel(II) synergistic catalysis.

Authors:  Xinyue Hu; Xiaoxue Tang; Xiying Zhang; Lili Lin; Xiaoming Feng
Journal:  Nat Commun       Date:  2021-05-21       Impact factor: 14.919

7.  Lanthanide complexes combined with chiral salen ligands: application in the enantioselective epoxidation reaction of α,β-unsaturated ketones.

Authors:  Xuexiu Xia; Chengrong Lu; Bei Zhao; Yingming Yao
Journal:  RSC Adv       Date:  2019-05-03       Impact factor: 4.036

8.  Sequential Conia-ene-type cyclization and Negishi coupling by cooperative functions of B(C6F5)3, ZnI2, Pd(PPh3)4 and an amine.

Authors:  Min Cao; Ahmet Yesilcimen; Soumil Prasad; Jason Genova; Tanner Myers; Masayuki Wasa
Journal:  Org Biomol Chem       Date:  2020-09-23       Impact factor: 3.876

9.  Asymmetric Synthesis of Spiropyrazolones by Sequential Organo- and Silver Catalysis.

Authors:  Daniel Hack; Alexander B Dürr; Kristina Deckers; Pankaj Chauhan; Nico Seling; Lukas Rübenach; Lucas Mertens; Gerhard Raabe; Franziska Schoenebeck; Dieter Enders
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-16       Impact factor: 15.336

10.  Radical asymmetric intramolecular α-cyclopropanation of aldehydes towards bicyclo[3.1.0]hexanes containing vicinal all-carbon quaternary stereocenters.

Authors:  Liu Ye; Qiang-Shuai Gu; Yu Tian; Xiang Meng; Guo-Cong Chen; Xin-Yuan Liu
Journal:  Nat Commun       Date:  2018-01-15       Impact factor: 14.919
  10 in total

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