Literature DB >> 15957893

Enantioselective rhodium enolate protonations. A new methodology for the synthesis of beta2-amino acids.

Mukund P Sibi1, Hiroto Tatamidani, Kalyani Patil.   

Abstract

[reaction: see text] Rhodium-catalyzed conjugate addition of an aryl boronic acid to alpha-methylamino acrylates followed by enantioselective protonation of the oxa-pi-allylrhodium intermediate provides access to aryl-substituted beta(2)-amino acids. The impact of the different variables of the reaction on the levels of enantioselectivity has been assessed.

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Year:  2005        PMID： 15957893      PMCID： PMC2596577          DOI： 10.1021/ol050630b

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


  20 in total

1.  Tandem 1,4-addition/enantioselective protonation catalyzed by rhodium complexes: efficient access to alpha-amino acids.

Authors:  Laure Navarre; Sylvain Darses; Jean-Pierre Genet
Journal:  Angew Chem Int Ed Engl       Date:  2004-01-30       Impact factor: 15.336

2.  Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds.

Authors:  Keith Fagnou; Mark Lautens
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

3.  Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions.

Authors:  Tamio Hayashi; Kaori Yamasaki
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

4.  Enantioselective H-atom transfer reactions: a new methodology for the synthesis of beta2-amino acids.

Authors:  Mukund P Sibi; Kalyani Patil
Journal:  Angew Chem Int Ed Engl       Date:  2004-02-27       Impact factor: 15.336

5.  Catalytic enantioselective synthesis of beta3-amino acids.

Authors:  Huw M L Davies; Chandrasekar Venkataramani
Journal:  Angew Chem Int Ed Engl       Date:  2002-06-17       Impact factor: 15.336

6.  The role of the achiral template in enantioselective transformations. Radical conjugate additions to alpha-methacrylates followed by hydrogen atom transfer.

Authors:  Mukund P Sibi; Justin B Sausker
Journal:  J Am Chem Soc       Date:  2002-02-13       Impact factor: 15.419

7.  BINOL-based diphosphonites as ligands in the asymmetric Rh-catalyzed conjugate addition of arylboronic acids.

Authors:  M T Reetz; D Moulin; A Gosberg
Journal:  Org Lett       Date:  2001-12-13       Impact factor: 6.005

8.  Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids. Arylrhodium, oxa-pi-allylrhodium, and hydroxorhodium intermediates.

Authors:  Tamio Hayashi; Makoto Takahashi; Yoshiaki Takaya; Masamichi Ogasawara
Journal:  J Am Chem Soc       Date:  2002-05-08       Impact factor: 15.419

9.  Three new cryptophycins from Nostoc sp. GSV 224.

Authors:  G V Subbaraju; T Golakoti; G M Patterson; R E Moore
Journal:  J Nat Prod       Date:  1997-03       Impact factor: 4.050

10.  Chiral biphenyl diphosphines for asymmetric catalysis: stereoelectronic design and industrial perspectives.

Authors:  Séverine Jeulin; Sébastien Duprat de Paule; Virginie Ratovelomanana-Vidal; Jean-Pierre Genêt; Nicolas Champion; Philippe Dellis
Journal:  Proc Natl Acad Sci U S A       Date:  2004-03-18       Impact factor: 11.205
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  10 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

2.  Enantioselective radical reactions. Evaluation of nitrogen protecting groups in the synthesis of beta-amino acids.

Authors:  Mukund P Sibi; Kalyani Patil
Journal:  Tetrahedron Asymmetry       Date:  2006-02-20

3.  Enantioselective synthesis of tryptophan derivatives by a tandem Friedel-Crafts conjugate addition/asymmetric protonation reaction.

Authors:  Madeleine E Kieffer; Lindsay M Repka; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2012-03-05       Impact factor: 15.419

4.  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

5.  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

6.  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

7.  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

8.  Preparation of tetrasubstituted olefins using mono or double aerobic direct C-H functionalization strategies: importance of steric effects.

Authors:  Nicolas Gigant; François Quintin; Jan-E Bäckvall
Journal:  J Org Chem       Date:  2015-02-16       Impact factor: 4.354

Review 9.  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

10.  Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride.

Authors:  Yiting Gu; Jack R Norton; Farbod Salahi; Vladislav G Lisnyak; Zhiyao Zhou; Scott A Snyder
Journal:  J Am Chem Soc       Date:  2021-06-18       Impact factor: 16.383
  10 in total

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