Literature DB >> 18429619

Lewis acid-Lewis base catalyzed enantioselective hetero-Diels-Alder reaction for direct access to delta-lactones.

Paolo S Tiseni1, René Peters.   

Abstract

A complex formed in situ from Er(OTf)3 and a simple commercially available norephedrine ligand promotes an unprecedented [4 + 2] cycloaddition of alpha,beta-unsaturated acid chlorides with a broad range of aromatic and heteroaromatic aldehydes by a cooperative bifunctional Lewis acid-Lewis base catalytic mode of action providing valuable delta-lactone building blocks with excellent enantioselectivity.

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Year:  2008        PMID: 18429619     DOI: 10.1021/ol800742d

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


  5 in total

1.  Catalytic, asymmetric reactions of ketenes and ketene enolates.

Authors:  Daniel H Paull; Anthony Weatherwax; Thomas Lectka
Journal:  Tetrahedron       Date:  2009-08-22       Impact factor: 2.457

Review 2.  Asymmetric Organocatalysis: The Emerging Utility of α,β-Unsaturated Acylammonium Salts.

Authors:  Sreekumar Vellalath; Daniel Romo
Journal:  Angew Chem Int Ed Engl       Date:  2016-09-21       Impact factor: 15.336

3.  Carbon-carbon bond activation of cyclobutenones enabled by the addition of chiral organocatalyst to ketone.

Authors:  Bao-Sheng Li; Yuhuang Wang; Zhichao Jin; Pengcheng Zheng; Rakesh Ganguly; Yonggui Robin Chi
Journal:  Nat Commun       Date:  2015-02-05       Impact factor: 14.919

4.  Cycloaddition of cyclobutenone and azomethine imine enabled by chiral isothiourea organic catalysts.

Authors:  Bao-Sheng Li; Yuhuang Wang; Zhichao Jin; Yonggui Robin Chi
Journal:  Chem Sci       Date:  2015-07-20       Impact factor: 9.825

5.  Cooperative Al(salen)-pyridinium catalysts for the asymmetric synthesis of trans-configured β-lactones by [2+2]-cyclocondensation of acylbromides and aldehydes: investigation of pyridinium substituent effects.

Authors:  Patrick Meier; Florian Broghammer; Katja Latendorf; Guntram Rauhut; René Peters
Journal:  Molecules       Date:  2012-06-12       Impact factor: 4.411

  5 in total

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