Literature DB >> 18582053

A Brønsted acid catalyst for the enantioselective protonation reaction.

Cheol Hong Cheon1, Hisashi Yamamoto.   

Abstract

A highly reactive and robust chiral Brønsted acid catalyst, chiral N-triflyl thiophosphoramide, was developed. The first metal-free Brønsted acid catalyzed enantioselective protonation reaction of silyl enol ethers was demonstrated using this chiral Brønsted acid catalyst. The catalyst loading could be reduced to 0.05 mol % without any deleterious effect on the enantioselectivity.

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Year:  2008        PMID: 18582053      PMCID: PMC2559973          DOI: 10.1021/ja8041542

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


  16 in total

1.  Enantioselective protonation of silyl enolates catalyzed by a BinapAgF complex.

Authors:  Akira Yanagisawa; Taichiro Touge; Takayoshi Arai
Journal:  Angew Chem Int Ed Engl       Date:  2005-02-25       Impact factor: 15.336

2.  Asymmetric Brønsted acid catalysis: enantioselective nucleophilic substitutions and 1,4-additions.

Authors:  Magnus Rueping; Boris J Nachtsheim; Stefan A Moreth; Michael Bolte
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Enantioselective 1,3-dipolar cycloaddition of nitrones with ethyl vinyl ether: the difference between Brønsted and Lewis acid catalysis.

Authors:  Peng Jiao; Daisuke Nakashima; Hisashi Yamamoto
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

4.  Organocatalytic enantioselective protonation of silyl enolates mediated by cinchona alkaloids and a latent source of HF.

Authors:  Thomas Poisson; Vincent Dalla; Francis Marsais; Georges Dupas; Sylvain Oudeyer; Vincent Levacher
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Enantioselective aza-Henry reaction with an N-sulfinyl urea organocatalyst.

Authors:  MaryAnn T Robak; Monica Trincado; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2007-11-16       Impact factor: 15.419

Review 6.  Small-molecule H-bond donors in asymmetric catalysis.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

7.  Chiral Brønsted acids in the catalytic asymmetric Nazarov cyclization--the first enantioselective organocatalytic electrocyclic reaction.

Authors:  Magnus Rueping; Winai Ieawsuwan; Andrey P Antonchick; Boris J Nachtsheim
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

8.  Design of chiral N-triflyl phosphoramide as a strong chiral Brønsted acid and its application to asymmetric Diels-Alder reaction.

Authors:  Daisuke Nakashima; Hisashi Yamamoto
Journal:  J Am Chem Soc       Date:  2006-08-02       Impact factor: 15.419

9.  Chiral Brønsted acid-catalyzed direct Mannich reactions via electrophilic activation.

Authors:  Daisuke Uraguchi; Masahiro Terada
Journal:  J Am Chem Soc       Date:  2004-05-05       Impact factor: 15.419

10.  High substrate/catalyst organocatalysis by a chiral Brønsted acid for an enantioselective aza-ene-type reaction.

Authors:  Masahiro Terada; Kyoko Machioka; Keiichi Sorimachi
Journal:  Angew Chem Int Ed Engl       Date:  2006-03-27       Impact factor: 15.336

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  27 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.  Chiral Brønsted acid from a cationic gold(I) complex: catalytic enantioselective protonation of silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Osamu Kanno; F Dean Toste
Journal:  J Am Chem Soc       Date:  2011-08-04       Impact factor: 15.419

3.  Syntheses of (+)-30-epi-, (-)-6-epi-, (±)-6,30-epi-13,14-Didehydroxyisogarcinol and (±)-6,30-epi-Garcimultiflorone A Utilizing Highly Diastereoselective, Lewis Acid-Controlled Cyclizations.

Authors:  Jonathan H Boyce; Vincent Eschenbrenner-Lux; John A Porco
Journal:  J Am Chem Soc       Date:  2016-10-27       Impact factor: 15.419

4.  Asymmetric olefin isomerization of butenolides via proton transfer catalysis by an organic molecule.

Authors:  Yongwei Wu; Ravi P Singh; Li Deng
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

5.  Development of a new Lewis base-tolerant chiral LBA and its application to catalytic asymmetric protonation reaction.

Authors:  Cheol Hong Cheon; Tatsushi Imahori; Hisashi Yamamoto
Journal:  Chem Commun (Camb)       Date:  2010-08-23       Impact factor: 6.222

6.  Development and mechanism of an enantioselective bromocycloetherification reaction via Lewis base/chiral Brønsted acid cooperative catalysis.

Authors:  Scott E Denmark; Matthew T Burk
Journal:  Chirality       Date:  2013-11-07       Impact factor: 2.437

7.  Enantioselective CuH-Catalyzed Hydroacylation Employing Unsaturated Carboxylic Acids as Aldehyde Surrogates.

Authors:  Yujing Zhou; Jeffrey S Bandar; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2017-06-06       Impact factor: 15.419

8.  Catalytic asymmetric cross-couplings of racemic alpha-bromoketones with arylzinc reagents.

Authors:  Pamela M Lundin; Jorge Esquivias; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

9.  Stereocontrolled cyanohydrin ether synthesis through chiral Brønsted acid-mediated vinyl ether hydrocyanation.

Authors:  Chunliang Lu; Xiaoge Su; Paul E Floreancig
Journal:  J Org Chem       Date:  2013-09-04       Impact factor: 4.354

10.  The mechanism and an improved asymmetric allylboration of ketones catalyzed by chiral biphenols.

Authors:  David S Barnett; Philip N Moquist; Scott E Schaus
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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