Literature DB >> 15382910

Organocatalytic asymmetric aza-Friedel-Crafts alkylation of furan.

Daisuke Uraguchi1, Keiichi Sorimachi, Masahiro Terada.   

Abstract

A new asymmetric entry of the 1,2-aza-Friedel-Crafts reaction catalyzed by a chiral phosphoric acid is described. The present reaction has provided an atom-economical route to furan-2-ylamine derivatives in a highly enantioselective fashion. The synthetic utility of these products was displayed by oxidative cleavage of the furan ring (aza-Achmatowicz reaction) to form a 1,4-dicarbonyl compound that could be further derivatized to a chiral gamma-butenolid.

Entities:  

Year:  2004        PMID： 15382910     DOI： 10.1021/ja046185h

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  21 in total

1.  Asymmetric cross-dehydrogenative coupling enabled by the design and application of chiral triazole-containing phosphoric acids.

Authors:  Andrew J Neel; Jörg P Hehn; Pascal F Tripet; F Dean Toste
Journal:  J Am Chem Soc       Date:  2013-09-11       Impact factor: 15.419

2.  Synthesis and Reactivity of α-Haloglycine Esters: Hyperconjugation in Action.

Authors:  Shyam S Samanta; Stéphane P Roche
Journal:  European J Org Chem       Date:  2019-08-24

3.  In Situ-Generated Glycinyl Chloroaminals for a One-Pot Synthesis of Non-proteinogenic α-Amino Esters.

Authors:  Shyam S Samanta; Stéphane P Roche
Journal:  J Org Chem       Date:  2017-08-04       Impact factor: 4.354

4.  Highly enantioselective trapping of zwitterionic intermediates by imines.

Authors:  Huang Qiu; Ming Li; Li-Qin Jiang; Feng-Ping Lv; Li Zan; Chang-Wei Zhai; Michael P Doyle; Wen-Hao Hu
Journal:  Nat Chem       Date:  2012-07-29       Impact factor: 24.427

5.  Chiral sulfinamidourea and strong Brønsted acid-cocatalyzed enantioselective Povarov reaction to access tetrahydroquinolines.

Authors:  Hao Xu; Hu Zhang; Eric N Jacobsen
Journal:  Nat Protoc       Date:  2014-07-10       Impact factor: 13.491

6.  Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization.

Authors:  Andy S Tsai; Michael E Tauchert; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2011-01-04       Impact factor: 15.419

7.  Chiral phosphoric acid catalyzed addition of dihydropyrans to N-acyl imines: stereocontrolled access to enantioenriched spirocyclic oxazoletetrahydropyrans with three contiguous stereocenters.

Authors:  Guilong Li; Matthew J Kaplan; Lukasz Wojtas; Jon C Antilla
Journal:  Org Lett       Date:  2010-05-07       Impact factor: 6.005

8.  Total synthesis of (+/-)- and (-)-actinophyllic acid.

Authors:  Connor L Martin; Larry E Overman; Jason M Rohde
Journal:  J Am Chem Soc       Date:  2010-04-07       Impact factor: 15.419

9.  Ag-catalyzed diastereo- and enantioselective vinylogous Mannich reactions of alpha-ketoimine esters. Development of a method and investigation of its mechanism.

Authors:  Laura C Wieland; Erika M Vieira; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

10.  Three-component Ag-catalyzed enantioselective vinylogous mannich and Aza-Diels-Alder reactions with alkyl-substituted aldehydes.

Authors:  Hiroki Mandai; Kyoko Mandai; Marc L Snapper; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2008-12-31       Impact factor: 15.419
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