Literature DB >> 16895388

Vanadium-catalyzed addition of propargyl alcohols and imines.

Barry M Trost1, Cheol K Chung.   

Abstract

A Mannich-type addition of propargylic alcohols and N-methoxycarbonylimines has been achieved by using a vanadium catalyst. The reactivity of the vanadium catalyst could be modulated by modifying the silanol ligands to avoid the background reaction. The strategy described herein provides an atom-economical access to beta-aryl-substituted Z-enones with an allylic amino functional group, which are not readily accessible with other methods.

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Year:  2006        PMID: 16895388      PMCID: PMC2529155          DOI: 10.1021/ja064011p

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


  6 in total

1.  Atom economy: aldol-type products by vanadium-catalyzed additions of propargyl alcohols and aldehydes.

Authors:  B M Trost; S Oi
Journal:  J Am Chem Soc       Date:  2001-02-14       Impact factor: 15.419

2.  Atom economy. Aldol-type products by vanadium-catalyzed additions of allenic alcohols and aldehydes.

Authors:  B M Trost; C Jonasson; M Wuchrer
Journal:  J Am Chem Soc       Date:  2001-12-19       Impact factor: 15.419

3.  Vanadium-catalyzed anti-selective additions of allenols to imines.

Authors:  Barry M Trost; Catrin Jonasson
Journal:  Angew Chem Int Ed Engl       Date:  2003-05-09       Impact factor: 15.336

4.  Enantioselective synthesis of propargylamines by copper-catalyzed addition of alkynes to enamines.

Authors:  Christopher Koradin; Kurt Polborn; Paul Knochel
Journal:  Angew Chem Int Ed Engl       Date:  2002-07-15       Impact factor: 15.336

5.  The atom economy--a search for synthetic efficiency.

Authors:  B M Trost
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728

6.  A mild C-O bond formation catalyzed by a rhenium-oxo complex.

Authors:  Benjamin D Sherry; Alexander T Radosevich; F Dean Toste
Journal:  J Am Chem Soc       Date:  2003-05-21       Impact factor: 15.419

  6 in total
  2 in total

1.  N-heterocyclic carbene-initiated alpha-acylvinyl anion reactivity: additions of alpha-hydroxypropargylsilanes to aldehydes.

Authors:  Troy E Reynolds; Charlotte A Stern; Karl A Scheidt
Journal:  Org Lett       Date:  2007-06-01       Impact factor: 6.005

2.  Catalytic enantioselective alpha-acylvinyl anion reactions of silyloxyallenes.

Authors:  Troy E Reynolds; Karl A Scheidt
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

  2 in total

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