Literature DB >> 20151675

N-Heterocyclic carbene catalyzed asymmetric hydration: direct synthesis of alpha-protio and alpha-deuterio alpha-chloro and alpha-fluoro carboxylic acids.

Harit U Vora1, Tomislav Rovis.   

Abstract

Asymmetric hydration of alpha,alpha-dichloro aldehydes and alpha-halo enals via a NHC-catalyzed redox process to yield enantioenriched alpha-chloro and alpha-fluoro carboxylic acids is described herein. The developed reaction allows for installation of an alpha-deuterium to give rise to enantioenriched alpha-deutero alpha-halo acids using D(2)O as the deuteron source.

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Year:  2010        PMID： 20151675      PMCID： PMC2839412          DOI： 10.1021/ja910281s

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


  25 in total

1.  Strategies for catalytic asymmetric electrophilic alpha halogenation of carbonyl compounds.

Authors:  Martin Oestreich
Journal:  Angew Chem Int Ed Engl       Date:  2005-04-15       Impact factor: 15.336

2.  N-heterocyclic carbene catalyzed C--C bond cleavage in redox esterifications of chiral formylcyclopropanes.

Authors:  Stephanie S Sohn; Jeffrey W Bode
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-11       Impact factor: 15.336

3.  Catalytic asymmetric synthesis of tertiary alkyl chlorides.

Authors:  Elaine C Lee; Kevin M McCauley; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

Review 4.  Modern synthetic methods for fluorine-substituted target molecules.

Authors:  Masaki Shimizu; Tamejiro Hiyama
Journal:  Angew Chem Int Ed Engl       Date:  2004-12-27       Impact factor: 15.336

Review 5.  Organocatalysis by N-heterocyclic carbenes.

Authors:  Dieter Enders; Oliver Niemeier; Alexander Henseler
Journal:  Chem Rev       Date:  2007-10-23       Impact factor: 60.622

6.  Redox economy in organic synthesis.

Authors:  Noah Z Burns; Phil S Baran; Reinhard W Hoffmann
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

7.  Enantioselective protonation of catalytically generated chiral enolates as an approach to the synthesis of alpha-chloroesters.

Authors:  Nathan T Reynolds; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2005-11-30       Impact factor: 15.419

8.  Catalytic, asymmetric alpha-chlorination of acid halides.

Authors:  Stefan France; Harald Wack; Andrew E Taggi; Ahmed M Hafez; Ty R Wagerle; Meha H Shah; Crystal L Dusich; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2004-04-07       Impact factor: 15.419

9.  Modified chiral triazolium salts for enantioselective benzoin cyclization of enolizable keto-aldehydes: synthesis of (+)-sappanone B.

Authors:  Hiroshi Takikawa; Keisuke Suzuki
Journal:  Org Lett       Date:  2007-06-09       Impact factor: 6.005

10.  Chiral NHC-catalyzed oxodiene Diels-Alder reactions with alpha-chloroaldehyde bisulfite salts.

Authors:  Ming He; Brendan J Beahm; Jeffrey W Bode
Journal:  Org Lett       Date:  2008-07-26       Impact factor: 6.005
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  18 in total

1.  Chiral N-heterocyclic carbene-catalyzed generation of ester enolate equivalents from {alpha},{beta}-unsaturated aldehydes for enantioselective Diels-Alder reactions.

Authors:  Juthanat Kaeobamrung; Marisa C Kozlowski; Jeffrey W Bode
Journal:  Proc Natl Acad Sci U S A       Date:  2010-10-25       Impact factor: 11.205

Review 2.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

3.  A biocatalytic method for the chemoselective aerobic oxidation of aldehydes to carboxylic acids.

Authors:  Tanja Knaus; Vasilis Tseliou; Luke D Humphreys; Nigel S Scrutton; Francesco G Mutti
Journal:  Green Chem       Date:  2018-07-10       Impact factor: 10.182

4.  Asymmetric N-Heterocyclic Carbene (NHC) Catalyzed Acyl Anion Reactivity.

Authors:  Harit U Vora; Tomislav Rovis
Journal:  Aldrichimica Acta       Date:  2011       Impact factor: 3.667

5.  Asymmetric NHC-catalyzed synthesis of α-fluoroamides from readily accessible α-fluoroenals.

Authors:  Philip Wheeler; Harit U Vora; Tomislav Rovis
Journal:  Chem Sci       Date:  2013-04       Impact factor: 9.825

6.  β-Carbon activation of saturated carboxylic esters through N-heterocyclic carbene organocatalysis.

Authors:  Zhenqian Fu; Jianfeng Xu; Tingshun Zhu; Wendy Wen Yi Leong; Yonggui Robin Chi
Journal:  Nat Chem       Date:  2013-07-21       Impact factor: 24.427

7.  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

8.  Late-stage diversification of chiral N-heterocyclic-carbene precatalysts for enantioselective homoenolate additions.

Authors:  Pinguan Zheng; Chenaimwoyo A Gondo; Jeffrey W Bode
Journal:  Chem Asian J       Date:  2010-12-22

9.  Exploiting Acyl and Enol Azolium Intermediates via NHeterocyclic Carbene Catalyzed Reactions of Alpha-Reducible Aldehydes.

Authors:  Harit U Vora; Philip Wheeler; Tomislav Rovis
Journal:  Adv Synth Catal       Date:  2012-04-19       Impact factor: 5.837

10.  Influence of Electronic Effects on the Reactivity of Triazolylidene-Boryl Radicals: Consequences for the use of N-Heterocyclic Carbene Boranes in Organic and Polymer Synthesis.

Authors:  Sofia Telitel; Anne-Laure Vallet; Darrin M Flanigan; Bernadette Graff; Fabrice Morlet-Savary; Tomislav Rovis; Jacques Lalevée; Emmanuel Lacôte
Journal:  Chemistry       Date:  2015-08-03       Impact factor: 5.236
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