Literature DB >> 17465559

Rhodium-catalyzed conjugate addition-enantioselective protonation: the synthesis of alpha,alpha'-dibenzyl esters.

Christopher G Frost1, Stephen D Penrose, Kim Lambshead, Paul R Raithby, John E Warren, Robert Gleave.   

Abstract

Alpha-benzyl acrylates, which are conveniently prepared from the corresponding aldehydes, can be employed as substrates in a tandem rhodium-catalyzed conjugate addition-enantioselective protonation protocol to afford enantiomerically enriched alpha,alpha'-dibenzyl esters. The synergistic effect of enantiopure ligand and proton source was rapidly optimized with use of a microwave reactor.

Entities:  

Year:  2007        PMID: 17465559     DOI: 10.1021/ol070603g

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


  7 in total

Review 1.  Enantioselective protonation.

Authors:  Justin T Mohr; Allen Y Hong; Brian M Stoltz
Journal:  Nat Chem       Date:  2009-08       Impact factor: 24.427

Review 2.  Controlled microwave heating in modern organic synthesis: highlights from the 2004-2008 literature.

Authors:  C Oliver Kappe; Doris Dallinger
Journal:  Mol Divers       Date:  2009-04-21       Impact factor: 2.943

3.  Rhodium(II)-catalyzed enantioselective C-H functionalization of indoles.

Authors:  Andrew DeAngelis; Valerie W Shurtleff; Olga Dmitrenko; Joseph M Fox
Journal:  J Am Chem Soc       Date:  2011-01-25       Impact factor: 15.419

4.  Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of enantiomerically enriched potassium β-trifluoroboratoamides with various aryl- and hetaryl chlorides.

Authors:  Gary A Molander; Inji Shin; Ludivine Jean-Gérard
Journal:  Org Lett       Date:  2010-10-01       Impact factor: 6.005

5.  Homogeneous pd-catalyzed enantioselective decarboxylative protonation.

Authors:  Smaranda C Marinescu; Toyoki Nishimata; Justin T Mohr; Brian M Stoltz
Journal:  Org Lett       Date:  2008-02-28       Impact factor: 6.005

6.  Rh(I)-bisphosphine-catalyzed asymmetric, intermolecular hydroheteroarylation of α-substituted acrylate derivatives.

Authors:  Claire M Filloux; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2014-12-29       Impact factor: 15.419

Review 7.  Conjugate addition-enantioselective protonation reactions.

Authors:  James P Phelan; Jonathan A Ellman
Journal:  Beilstein J Org Chem       Date:  2016-06-15       Impact factor: 2.883

  7 in total

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