Literature DB >> 19256562

Catalytic enantioselective synthesis of tetrahydrofurans: a dynamic kinetic asymmetric [3 + 2] cycloaddition of racemic cyclopropanes and aldehydes.

Andrew T Parsons1, Jeffrey S Johnson.   

Abstract

A highly diastereoselective dynamic kinetic asymmetric transformation of racemic 1,1-cyclopropane diesters to prepare enantioenriched tetrahydrofuran (THF) derivatives has been developed. Asymmetric [3 + 2] cycloaddition of activated donor-acceptor (D-A) cyclopropanes and aldehydes catalyzed by ((t)Bu-pybox)MgI(2) gives THF products in good to excellent yields (48-92%) as single diastereomers with er's up to 97:3. Aryl, cinnamyl, and aliphatic aldehydes are competent dipolarophiles for this transformation.

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Year:  2009        PMID： 19256562     DOI： 10.1021/ja809873u

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


  23 in total

1.  Asymmetric synthesis of methylenetetrahydrofurans by palladium-catalyzed [3 + 2] cycloaddition of trimethylenemethane with aldehydes--a novel ligand design.

Authors:  Barry M Trost; Dustin A Bringley; Steven M Silverman
Journal:  J Am Chem Soc       Date:  2011-05-03       Impact factor: 15.419

2.  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

3.  Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones.

Authors:  Adrian G Amador; Evan M Sherbrook; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2016-03-29       Impact factor: 15.419

4.  Palladium-catalyzed diastereo- and enantioselective synthesis of substituted cyclopentanes through a dynamic kinetic asymmetric formal [3+2]-cycloaddition of vinyl cyclopropanes and alkylidene azlactones.

Authors:  Barry M Trost; Patrick J Morris
Journal:  Angew Chem Int Ed Engl       Date:  2011-05-23       Impact factor: 15.336

5.  Palladium-catalyzed diastereo- and enantioselective formal [3 + 2]-cycloadditions of substituted vinylcyclopropanes.

Authors:  Barry M Trost; Patrick J Morris; Simon J Sprague
Journal:  J Am Chem Soc       Date:  2012-10-10       Impact factor: 15.419

6.  Enantioselective synthesis of 2,2-disubstituted tetrahydrofurans: palladium-catalyzed [3+2] cycloadditions of trimethylenemethane with ketones.

Authors:  Barry M Trost; Dustin A Bringley
Journal:  Angew Chem Int Ed Engl       Date:  2013-03-12       Impact factor: 15.336

7.  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

8.  Lewis acid mediated (3 + 2) cycloadditions of donor-acceptor cyclopropanes with heterocumulenes.

Authors:  Alexander F G Goldberg; Nicholas R O'Connor; Robert A Craig; Brian M Stoltz
Journal:  Org Lett       Date:  2012-10-09       Impact factor: 6.005

9.  Dynamic kinetic asymmetric transformations of β-stereogenic α-ketoesters by direct aldolization.

Authors:  Michael T Corbett; Jeffrey S Johnson
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-12       Impact factor: 15.336

10.  Enantioselective Ruthenium-Catalyzed Benzocyclobutenone-Ketol Cycloaddition: Merging C-C Bond Activation and Transfer Hydrogenative Coupling for Type II Polyketide Construction.

Authors:  Brett R Ambler; Ben W H Turnbull; Sankar Rao Suravarapu; Maulen M Uteuliyev; Nancy O Huynh; Michael J Krische
Journal:  J Am Chem Soc       Date:  2018-07-11       Impact factor: 15.419
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