Literature DB >> 19681591

Enantioselective synthesis of beta-trifluoromethyl-beta-lactones via NHC-catalyzed ketene-ketone cycloaddition reactions.

Xiao-Na Wang1, Pan-Lin Shao, Hui Lv, Song Ye.   

Abstract

The highly diastereo- and enantioselective synthesis of beta-trifluoromethyl-beta-lactones bearing two contiguous stereocenters was realized by chiral N-heterocyclic carbene-catalyzed formal cycloaddition reaction of alkyl(aryl)ketenes and trifluoromethyl ketones.

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Year:  2009        PMID： 19681591     DOI： 10.1021/ol901290z

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


  11 in total

1.  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

2.  Double diastereoselective, nucleophile-catalyzed aldol lactonizations (NCAL) leading to beta-lactone fused carbocycles and extensions to beta-lactone fused tetrahydrofurans.

Authors:  Kay A Morris; Kevin M Arendt; Seong Ho Oh; Daniel Romo
Journal:  Org Lett       Date:  2010-09-03       Impact factor: 6.005

3.  Rubesanolides A and B: diterpenoids from Isodon rubescens.

Authors:  Juan Zou; Lutai Pan; Qiji Li; Junhua Zhao; Jianxin Pu; Ping Yao; Ningbo Gong; Yang Lu; Tamara P Kondratyuk; John M Pezzuto; Harry H S Fong; Hongjie Zhang; Handong Sun
Journal:  Org Lett       Date:  2011-02-18       Impact factor: 6.005

4.  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

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.  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

7.  NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides.

Authors:  Alyn T Davies; Mark D Greenhalgh; Alexandra M Z Slawin; Andrew D Smith
Journal:  Beilstein J Org Chem       Date:  2020-06-30       Impact factor: 2.883

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.  Mechanism and stereoselectivity in NHC-catalyzed β-functionalization of saturated carboxylic ester.

Authors:  Yan Li; Zhiqiang Zhang
Journal:  RSC Adv       Date:  2019-03-06       Impact factor: 4.036

10.  One-pot tandem cyclization of enantiopure asymmetric cis-2,5-disubstituted pyrrolidines: Facile access to chiral 10-heteroazatriquinanes.

Authors:  Ping-An Wang; Sheng-Yong Zhang; Henri B Kagan
Journal:  Beilstein J Org Chem       Date:  2013-02-07       Impact factor: 2.883
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