Literature DB >> 21877756

Formal Diels-Alder reactions of chalcones and formylcyclopropanes catalyzed by chiral N-heterocyclic carbenes.

Hui Lv1, Junming Mo, Xinqiang Fang, Yonggui Robin Chi.   

Abstract

Highly enantioselective (formal) hetero-Diels-Alder reactions between chalcones and formylcyclopropanes are disclosed. The challenging N-heterocyclic carbene (NHC)-bounded enolate intermediates from formylcyclopropanes were captured for new C-C bond forming reactions. The reaction products were obtained with high diastereo- and enantioselectivities and could be easily transformed to optically pure multisubstituted cyclohexane derivatives.
© 2011 American Chemical Society

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Year:  2011        PMID： 21877756     DOI： 10.1021/ol202250s

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


  6 in total

1.  Oxyanion steering and CH-π interactions as key elements in an N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition.

Authors:  Scott E Allen; Jessada Mahatthananchai; Jeffrey W Bode; Marisa C Kozlowski
Journal:  J Am Chem Soc       Date:  2012-07-16       Impact factor: 15.419

2.  Metalloradical activation of α-formyldiazoacetates for the catalytic asymmetric radical cyclopropanation of alkenes.

Authors:  Xue Xu; Yong Wang; Xin Cui; Lukasz Wojtas; X Peter Zhang
Journal:  Chem Sci       Date:  2017-03-31       Impact factor: 9.825

3.  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

4.  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

5.  Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes.

Authors:  Xiaoxiao Song; Qijian Ni; Chen Zhu; Gerhard Raabe; Dieter Enders
Journal:  Synthesis (Stuttg)       Date:  2014-11-06       Impact factor: 3.157

6.  An Unexpected Inactivation of N-Heterocyclic Carbene Organic Catalyst by 1-Methylcyclopropylcarbaldehyde and 2,2,2-Trifluoroacetophenone.

Authors:  Yanling Chen; Jie Lv; Xuling Pan; Zhichao Jin
Journal:  Front Chem       Date:  2022-03-24       Impact factor: 5.221
  6 in total

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