Literature DB >> 19353613

Palladium-catalyzed insertion of alpha-diazoesters into vinyl halides to generate alpha,beta-unsaturated gamma-amino esters.

Romas Kudirka1, Sean K J Devine, Christopher S Adams, David L Van Vranken.   

Abstract

As easy as 1, 2, 3: A palladium-catalyzed three-component coupling generates alpha,beta-unsaturated gamma-amino acids in a single step (see scheme). The reaction is believed to involve migration of a vinyl substituent to a highly electrophilic palladium carbene. Unlike previous synthetic approaches, this synthesis provides access to gamma-amino acids with non-natural side chains.

Entities:  

Year:  2009        PMID: 19353613     DOI: 10.1002/anie.200805483

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  A palladium-catalyzed three-component cross-coupling of conjugated dienes or terminal alkenes with vinyl triflates and boronic acids.

Authors:  Longyan Liao; Ranjan Jana; Kaveri Balan Urkalan; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2011-03-30       Impact factor: 15.419

3.  Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.

Authors:  Matthew S McCammant; Longyan Liao; Matthew S Sigman
Journal:  J Am Chem Soc       Date:  2013-03-12       Impact factor: 15.419

4.  Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds.

Authors:  Gui Chen; Jinshuai Song; Yinghua Yu; Xuesong Luo; Chunsen Li; Xueliang Huang
Journal:  Chem Sci       Date:  2015-12-14       Impact factor: 9.825

5.  Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from sp2-carbon.

Authors:  Ge Zhang; Yi-Kang Song; Fang Zhang; Ze-Jian Xue; Meng-Yao Li; Gui-Shan Zhang; Bin-Bin Zhu; Jing Wei; Chunsen Li; Chen-Guo Feng; Guo-Qiang Lin
Journal:  Nat Commun       Date:  2021-02-01       Impact factor: 14.919

6.  Pd-Catalyzed Dynamic Kinetic Asymmetric Cross-Coupling of Heterobiaryl Bromides with N-Tosylhydrazones.

Authors:  Shivashankar Kattela; Carlos Roque D Correia; Abel Ros; Valentín Hornillos; Javier Iglesias-Sigüenza; Rosario Fernández; José M Lassaletta
Journal:  Org Lett       Date:  2022-05-23       Impact factor: 6.072

  6 in total

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