Literature DB >> 18816140

Formal cycloaddition of disubstituted ketenes with 2-oxoaldehydes catalyzed by chiral N-heterocyclic carbenes.

Lin He1, Hui Lv, Yan-Rong Zhang, Song Ye.   

Abstract

Chiral N-hetereocyclic carbenes were found to be efficient catalysts for the formal [2 + 2] cycloaddition reactions of alkyl(aryl)ketenes with 2-oxoaldehydes to afford beta-lactones with alpha-quaternary-beta-tertiary stereocenters in high yields with good diastereoselectivities and excellent enantioselectivities (up to 99% ee). Both alkyl(aryl)ketenes and diarylketene worked well in this reaction.

Entities:  

Mesh：

Substances：

Year:  2008        PMID： 18816140     DOI： 10.1021/jo801494f

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  10 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

2.  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

3.  Catalytic Kinetic Resolution of a Dynamic Racemate: Highly Stereoselective β-Lactone Formation by N-Heterocyclic Carbene Catalysis.

Authors:  Ryne C Johnston; Daniel T Cohen; Chad C Eichman; Karl A Scheidt; Paul Ha-Yeon Cheong
Journal:  Chem Sci       Date:  2014-05-01       Impact factor: 9.825

4.  Asymmetric N-heterocyclic carbene catalyzed addition of enals to nitroalkenes: controlling stereochemistry via the homoenolate reactivity pathway to access δ-lactams.

Authors:  Nicholas A White; Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2013-05-28       Impact factor: 15.419

5.  Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral.

Authors:  James J Douglas; Gwydion Churchill; Alexandra M Z Slawin; David J Fox; Andrew D Smith
Journal:  Chemistry       Date:  2015-09-25       Impact factor: 5.236

6.  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

7.  Carbene catalyzed umpolung of α,β-enals: a reactivity study of diamino dienols vs. azolium enolates, and the characterization of advanced reaction intermediates.

Authors:  Veera Reddy Yatham; Jörg-M Neudörfl; Nils E Schlörer; Albrecht Berkessel
Journal:  Chem Sci       Date:  2015-04-30       Impact factor: 9.825

8.  A tandem dearomatization/rearomatization strategy: enantioselective N-heterocyclic carbene-catalyzed α-arylation.

Authors:  Zijun Wu; Jian Wang
Journal:  Chem Sci       Date:  2018-12-27       Impact factor: 9.825

9.  The Role of the Fused Ring in Bicyclic Triazolium Organocatalysts: Kinetic, X-ray, and DFT Insights.

Authors:  Jiayun Zhu; Inmaculada Moreno; Peter Quinn; Dmitry S Yufit; Lijuan Song; Claire M Young; Zhuan Duan; Andrew R Tyler; Paul G Waddell; Michael J Hall; Michael R Probert; Andrew D Smith; AnnMarie C O'Donoghue
Journal:  J Org Chem       Date:  2022-03-01       Impact factor: 4.354

10.  Isothiourea-Catalyzed [2 + 2] Cycloaddition of C(1)-Ammonium Enolates and N-Alkyl Isatins.

Authors:  Yusra Abdelhamid; Kevin Kasten; Joanne Dunne; Will C Hartley; Claire M Young; David B Cordes; Alexandra M Z Slawin; Sean Ng; Andrew D Smith
Journal:  Org Lett       Date:  2022-07-18       Impact factor: 6.072
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.