Literature DB >> 14510565

Synthesis of octahydroquinolines through the Lewis acid catalyzed reaction of vinyl allenes and imines.

David Regás1, María M Afonso, Matías L Rodríguez, J Antonio Palenzuela.   

Abstract

The reaction of vinyl allenes with imines under Lewis acid catalysis has been explored. Vinyl allenes in which the allenic portion of the molecule is tri- or tetrasubstituted gave octahydroquinoline derivatives as single isomers together with a minor compound formed by an ene reaction of the imine with the allene. Compounds in which the allene is 1,3-disubstituted do not react under the conditions assayed.

Entities:  

Year:  2003        PMID： 14510565     DOI： 10.1021/jo034480z

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


  4 in total

1.  N-isopropylidene-N'-2-nitrobenzenesulfonyl hydrazine, a reagent for reduction of alcohols via the corresponding monoalkyl diazenes.

Authors:  Mohammad Movassaghi; Omar K Ahmad
Journal:  J Org Chem       Date:  2007-02-03       Impact factor: 4.354

2.  Low temperature organocopper-mediated two-component cross coupling/cycloisomerization approach toward N-fused heterocycles.

Authors:  Dmitri Chernyak; Surendra Babu Gadamsetty; Vladimir Gevorgyan
Journal:  Org Lett       Date:  2008-05-08       Impact factor: 6.005

3.  Allenyl azide cycloaddition chemistry. Synthesis of annelated indoles from 2-(allenyl)phenyl azide substrates.

Authors:  Ken S Feldman; Malliga R Iyer; D Keith Hester
Journal:  Org Lett       Date:  2006-07-06       Impact factor: 6.005

4.  Regio- and Stereoselective Direct Cross-Coupling of Aromatic Imines with Allenic Alcohols.

Authors:  Martin McLaughlin; Heidi L Shimp; Raul Navarro; Glenn C Micalizio
Journal:  Synlett       Date:  2008-03-01       Impact factor: 2.454
  4 in total

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