Literature DB >> 18549233

Catalytic asymmetric stetter reaction onto vinylphosphine oxides and vinylphosphonates.

Steven C Cullen1, Tomislav Rovis.   

Abstract

An intramolecular Stetter reaction of vinylphosphine oxides and vinylphosphonates has been developed. Treatment of an aldehyde with a nucleophilic N-heterocyclic carbene catalyst allows for addition of an acyl anion equivalent into a vinylphosphine oxide or vinylphosphonate Michael acceptor in yields up to 99% and ee values up to 96%.

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Year:  2008        PMID: 18549233      PMCID: PMC2746454          DOI: 10.1021/ol801047k

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


  27 in total

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5.  Asymmetric hydrogenation of heteroaromatic compounds.

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6.  Enantioselective synthesis of P-stereogenic alkynylphosphine oxides by Rh-catalyzed [2+2+2] cycloaddition.

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7.  N-heterocyclic carbenes as organocatalysts.

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8.  Synthesis of glycophostones: cyclic phosphonate analogues of biologically relevant sugars

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Journal:  J Org Chem       Date:  2000-05-09       Impact factor: 4.354

9.  Diastereoselective synthesis of 2-amino-4-phosphonobutanoic acids by conjugate addition of lithiated Schöllkopf's bislactim ethers to vinylphosphonates.

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10.  Asymmetric synthesis of hydrobenzofuranones via desymmetrization of cyclohexadienones using the intramolecular Stetter reaction.

Authors:  Qin Liu; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419

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  6 in total

Review 1.  Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes.

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Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

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

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

3.  The Catalytic Asymmetric Intramolecular Stetter Reaction.

Authors:  Javier Read de Alaniz; Tomislav Rovis
Journal:  Synlett       Date:  2009-05       Impact factor: 2.454

4.  N-heterocyclic carbene and Brønsted acid cooperative catalysis: asymmetric synthesis of trans-γ-lactams.

Authors:  Xiaodan Zhao; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2011-07-25       Impact factor: 15.419

5.  Nucleophilic carbene catalyzed synthesis of 1,2 amino alcohols via azidation of epoxy aldehydes.

Authors:  Harit U Vora; Johannah R Moncecchi; Oleg Epstein; Tomislav Rovis
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

6.  Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation-cyclization cascade mediated by K2S2O8.

Authors:  Qiang Liu; Weibang Lu; Guanqun Xie; Xiaoxia Wang
Journal:  Beilstein J Org Chem       Date:  2020-08-12       Impact factor: 2.883

  6 in total

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