Literature DB >> 25155478

Stereoselective synthesis of aryl cyclopentene scaffolds by Heck-Matsuda desymmetrization of 3-cyclopentenol.

Ricardo A Angnes1, Juliana M Oliveira, Caio C Oliveira, Nelson C Martins, Carlos Roque D Correia.   

Abstract

A new enantioselective Heck-Matsuda desymmetrization reaction was accomplished by using 3-cyclopentenol to produce chiral five-membered 4-aryl cyclopentenol scaffolds in good yields and high ee's, together with some 3-aryl-cyclopentanones as minor products. Mechanistically, the hydroxyl group of 3-cyclopentenol acts as a directing group and is responsible for the cis- arrangement in the formation of the 4-aryl-cyclopentenols.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Heck reaction; aryldiazonium salts; chiral N,N ligands; desymmetrization; palladium

Year:  2014        PMID： 25155478     DOI： 10.1002/chem.201404159

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  5 in total

1.  Relative reactivity of alkenyl alcohols in the palladium-catalyzed redox-relay Heck reaction.

Authors:  Margaret J Hilton; Bin Cheng; Benjamin R Buckley; Liping Xu; Olaf Wiest; Matthew S Sigman
Journal:  Tetrahedron       Date:  2015-09-16       Impact factor: 2.457

2.  Enantioselective Heck-Matsuda Arylations through Chiral Anion Phase-Transfer of Aryl Diazonium Salts.

Authors:  Carolina M Avila; Jigar S Patel; Yernaidu Reddi; Masato Saito; Hosea M Nelson; Hunter P Shunatona; Matthew S Sigman; Raghavan B Sunoj; F Dean Toste
Journal:  Angew Chem Int Ed Engl       Date:  2017-04-18       Impact factor: 15.336

3.  Palladium-Catalyzed Enantioselective Redox-Relay Heck Arylation of 1,1-Disubstituted Homoallylic Alcohols.

Authors:  Zhi-Min Chen; Margaret J Hilton; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2016-09-01       Impact factor: 15.419

4.  Access to enantioenriched 2,3- and 2,5-dihydrofurans with a fully substituted C2 stereocenter by Pd-catalyzed asymmetric intermolecular Heck reaction.

Authors:  Gustavo M Borrajo-Calleja; Vincent Bizet; Thomas Bürgi; Clément Mazet
Journal:  Chem Sci       Date:  2015-06-03       Impact factor: 9.825

5.  Direct access to tetrasubstituted cyclopentenyl scaffolds through a diastereoselective isocyanide-based multicomponent reaction.

Authors:  Vitor A Fernandes; Rafaely N Lima; Yoisel B Broterson; Meire Y Kawamura; Radell Echemendía; Alexander F de la Torre; Marco A B Ferreira; Daniel G Rivera; Marcio W Paixão
Journal:  Chem Sci       Date:  2021-09-16       Impact factor: 9.825
  5 in total

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