Literature DB >> 28467706

Carbon-Nitrogen Bond Formation via the Vanadium Oxo Catalyzed Sigmatropic Functionalization of Allenols.

Barry M Trost1, Jacob S Tracy1.   

Abstract

A vanadium catalyzed 1,3-rearrangement of allenols to form transient vanadium enolates that selectively couple with electrophilic nitrogen sources is reported even in the presence of competing simple protonation and Alder-ene pathways. Hydrazine products can be cyclized in a 6-endo-trig fashion which, upon reductive cleavage of the N-N bond, yield 1,4-diamines. Additionally, cleavage of the N-N bond before cyclization can be achieved to form β-hydroxy amines, a common structural motif of biologically active compounds.

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Year:  2017        PMID： 28467706      PMCID： PMC5726861          DOI： 10.1021/acs.orglett.7b00961

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


  16 in total

1.  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

2.  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

Review 3.  The direct catalytic asymmetric aldol reaction.

Authors:  Barry M Trost; Cheyenne S Brindle
Journal:  Chem Soc Rev       Date:  2010-02-17       Impact factor: 54.564

4.  Contemporaneous Dual Catalysis: Aldol Products from Non-Carbonyl Substrates.

Authors:  Barry M Trost; Jacob S Tracy
Journal:  Chemistry       Date:  2015-09-03       Impact factor: 5.236

Review 5.  Making carbon-nitrogen bonds in biological and chemical synthesis.

Authors:  Ryan Hili; Andrei K Yudin
Journal:  Nat Chem Biol       Date:  2006-06       Impact factor: 15.040

Review 6.  Asymmetric enamine catalysis.

Authors:  Santanu Mukherjee; Jung Woon Yang; Sebastian Hoffmann; Benjamin List
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

7.  The advent and development of organocatalysis.

Authors:  David W C MacMillan
Journal:  Nature       Date:  2008-09-18       Impact factor: 49.962

8.  How easy are the syntheses of allenes?

Authors:  Shichao Yu; Shengming Ma
Journal:  Chem Commun (Camb)       Date:  2011-03-15       Impact factor: 6.222

9.  Enamine-based organocatalysis with proline and diamines: the development of direct catalytic asymmetric Aldol, Mannich, Michael, and Diels-alder reactions.

Authors:  Wolfgang Notz; Fujie Tanaka; Carlos F Barbas
Journal:  Acc Chem Res       Date:  2004-08       Impact factor: 22.384

10.  Aryldiones incorporating a [1,4,5]oxadiazepane ring. Part I: Discovery of the novel cereal herbicide pinoxaden.

Authors:  Michel Muehlebach; Manfred Boeger; Fredrik Cederbaum; Derek Cornes; Adrian A Friedmann; Jutta Glock; Thierry Niderman; André Stoller; Trixie Wagner
Journal:  Bioorg Med Chem       Date:  2009-01-03       Impact factor: 3.641
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  4 in total

1.  A distal vinyl shift (DVS) through quadruple domino reaction: synthesis of N-vinyl benzoheterocyclic scaffolds.

Authors:  Manickam Bakthadoss; Mohammad Mushaf
Journal:  RSC Adv       Date:  2018-03-28       Impact factor: 4.036

2.  Ruthenium-catalyzed, site-selective C-H activation: access to C5-substituted azaflavanone.

Authors:  Manickam Bakthadoss; Tadiparthi Thirupathi Reddy; Duddu S Sharada
Journal:  RSC Adv       Date:  2020-08-26       Impact factor: 3.361

3.  Direct catalytic enantioselective amination of ketones for the formation of tri- and tetrasubstituted stereocenters.

Authors:  B M Trost; J S Tracy; T Saget
Journal:  Chem Sci       Date:  2018-02-14       Impact factor: 9.825

Review 4.  Synergistic Effects of Heavy Metals and Pesticides in Living Systems.

Authors:  Nitika Singh; Vivek Kumar Gupta; Abhishek Kumar; Bechan Sharma
Journal:  Front Chem       Date:  2017-10-11       Impact factor: 5.221
  4 in total

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