Literature DB >> 21709880

Chiral N-heterocyclic carbene catalyzed annulation of α,β-unsaturated aldehydes with 1,3-dicarbonyls.

Zhi-Qiang Zhu1, Xing-Liang Zheng, Ning-Fei Jiang, Xiaolong Wan, Ji-Chang Xiao.   

Abstract

Chiral N-heterocyclic carbene catalyzed annulations of ynals and enals with 1,3-dicarbonyls have been described. The two reactions provided direct and efficient methods for enantioselective synthesis of functionalized dihydropyranones. Comparatively, the reactions starting from ynals were atom-economical; furthermore the reactions of enals demonstrated broader substrate compatibility. This journal is © The Royal Society of Chemistry 2011

Entities:  

Year:  2011        PMID： 21709880     DOI： 10.1039/c1cc12778k

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  10 in total

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

Authors:  Darrin M Flanigan; Fedor Romanov-Michailidis; Nicholas A White; Tomislav Rovis
Journal:  Chem Rev       Date:  2015-05-20       Impact factor: 60.622

2.  Chiral N-Heterocyclic Carbene Catalyzed Annulations of Enals and Ynals with Stable Enols: A Highly Enantioselective Coates-Claisen Rearrangement.

Authors:  Jessada Mahatthananchai; Juthanat Kaeobamrung; Jeffrey W Bode
Journal:  ACS Catal       Date:  2012-02-29       Impact factor: 13.084

3.  Electroredox carbene organocatalysis with iodide as promoter.

Authors:  Peng Zhou; Wenchang Li; Jianyong Lan; Tingshun Zhu
Journal:  Nat Commun       Date:  2022-07-02       Impact factor: 17.694

4.  A C1-symmetric N-heterocyclic carbene catalysed oxidative spiroannulation of isatin-derived enals: highly enantioselective synthesis of spirooxindole δ-lactones.

Authors:  Jun-Bing Lin; Xi-Na Cheng; Xiao-Dong Tian; Guo-Qiang Xu; Yong-Chun Luo; Peng-Fei Xu
Journal:  RSC Adv       Date:  2018-04-24       Impact factor: 4.036

5.  A Computational Study of the Origin of Stereoinduction in NHC-Catalyzed Annulation Reactions of α,β-Unsaturated Acyl Azoliums.

Authors:  Eirik Lyngvi; Jeffrey W Bode; Franziska Schoenebeck
Journal:  Chem Sci       Date:  2012-03-01       Impact factor: 9.825

6.  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

7.  A cooperative N-heterocyclic carbene/chiral phosphate catalysis system for allenolate annulations.

Authors:  Anna Lee; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2014-06-04       Impact factor: 15.336

8.  NHC-Catalyzed Asymmetric Synthesis of Functionalized Succinimides from Enals and α-Ketoamides.

Authors:  Lei Wang; Qijian Ni; Marcus Blümel; Tao Shu; Gerhard Raabe; Dieter Enders
Journal:  Chemistry       Date:  2015-04-15       Impact factor: 5.236

9.  N-Heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindoles and enals: cross coupling of homoenolate and enolate.

Authors:  Xiang-Yu Chen; Kun-Quan Chen; De-Qun Sun; Song Ye
Journal:  Chem Sci       Date:  2016-11-09       Impact factor: 9.825

10.  Enantioselective annulation of enals with 2-naphthols by triazolium salts derived from l-phenylalanine.

Authors:  Guo-Tai Li; Qing Gu; Shu-Li You
Journal:  Chem Sci       Date:  2015-04-30       Impact factor: 9.825
  10 in total

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