Literature DB >> 18656948

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

Ming He1, Brendan J Beahm, Jeffrey W Bode.   

Abstract

Alpha-chloroaldehyde bisulfite adducts were successfully employed in chiral NHC-catalyzed hetero-Diels-Alder reactions with various oxodienes under biphasic reaction conditions with high levels of enantioselectivity. This new protocol makes possible enantioselective additions from commercially available chloroacetaldehyde sodium bisulfite and demonstrates that this unique class of catalysts readily tolerates aqueous conditions.

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Year:  2008        PMID： 18656948      PMCID： PMC2728680          DOI： 10.1021/ol801502h

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


  32 in total

1.  Chiral N-heterocyclic carbene catalyzed, enantioselective oxodiene Diels-Alder reactions with low catalyst loadings.

Authors:  Ming He; Gerson J Uc; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2006-11-29       Impact factor: 15.419

2.  Iridium-catalyzed enantioselective synthesis of allylic alcohols: silanolates as hydroxide equivalents.

Authors:  Isabelle Lyothier; Christian Defieber; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2006-09-18       Impact factor: 15.336

3.  Enantioselective, cyclopentene-forming annulations via NHC-catalyzed benzoin-oxy-cope reactions.

Authors:  Pei-Chen Chiang; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  J Am Chem Soc       Date:  2007-03-03       Impact factor: 15.419

4.  Iridium-catalyzed synthesis of primary allylic amines from allylic alcohols: sulfamic acid as ammonia equivalent.

Authors:  Christian Defieber; Martin A Ariger; Patricia Moriel; Erick M Carreira
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

5.  Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines.

Authors:  Junji Itoh; Kohei Fuchibe; Takahiko Akiyama
Journal:  Angew Chem Int Ed Engl       Date:  2006-07-17       Impact factor: 15.336

6.  A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes.

Authors:  Eric M Phillips; Manabu Wadamoto; Audrey Chan; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

7.  Catalytic asymmetric inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-dienes.

Authors:  Jorge Esquivias; Ramón Gómez Arrayás; Juan C Carretero
Journal:  J Am Chem Soc       Date:  2007-02-14       Impact factor: 15.419

8.  Chiral Brønsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction.

Authors:  Takahiko Akiyama; Hisashi Morita; Kohei Fuchibe
Journal:  J Am Chem Soc       Date:  2006-10-11       Impact factor: 15.419

9.  Catalytic, enantioselective bifunctional inverse electron demand hetero-Diels-Alder reactions of ketene enolates and o-benzoquinone diimides.

Authors:  Ciby J Abraham; Daniel H Paull; Michael T Scerba; James W Grebinski; Thomas Lectka
Journal:  J Am Chem Soc       Date:  2006-10-18       Impact factor: 15.419

10.  Catalytic Synthesis of gamma-Lactams via direct annulations of enals and N-sulfonylimines.

Authors:  Ming He; Jeffrey W Bode
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005
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  9 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

2.  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

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

Authors:  Harit U Vora; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2010-03-10       Impact factor: 15.419

4.  Formal synthesis of salinosporamide A via NHC-catalyzed intramolecular lactonization.

Authors:  Justin R Struble; Jeffrey W Bode
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

5.  Metal-free catalytic C-Si bond formation in an aqueous medium. Enantioselective NHC-catalyzed silyl conjugate additions to cyclic and acyclic α,β-unsaturated carbonyls.

Authors:  Jeannette M O'Brien; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2011-04-27       Impact factor: 15.419

6.  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

7.  N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes.

Authors:  Xiaodan Zhao; Kyle E Ruhl; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2012-11-04       Impact factor: 15.336

8.  NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.

Authors:  Alyn T Davies; Mark D Greenhalgh; Alexandra M Z Slawin; Andrew D Smith
Journal:  Beilstein J Org Chem       Date:  2020-06-30       Impact factor: 2.883

9.  A Desilylative Approach to Alkyl Substituted C(1)-Ammonium Enolates: Application in Enantioselective [2+2] Cycloadditions.

Authors:  Yihong Wang; Claire M Young; Honglei Liu; Will C Hartley; Max Wienhold; David B Cordes; Alexandra M Z Slawin; Andrew D Smith
Journal:  Angew Chem Int Ed Engl       Date:  2022-08-08       Impact factor: 16.823
  9 in total

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