Literature DB >> 16316217

Zirconium-mediated SN2' substitution of allylic ethers: regio- and stereospecific formation of protected allylic amines.

Gojko Lalic1, Suzanne A Blum, Robert G Bergman.   

Abstract

A new zirconium-mediated, regio- and stereospecific SN2' substitution of allylic ethers with a nitrogen nucleophile has been developed. Cbz-protected amine products were isolated in high yield from reactions with a wide range of Z allylic ethers. A mechanism of the allylic substitution consistent with the results of the kinetics and kinetic isotope effect studies was proposed.

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Year:  2005        PMID： 16316217      PMCID： PMC2528547          DOI： 10.1021/ja056132f

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


  5 in total

1.  Stereospecific and stereodivergent construction of quaternary carbon centers through switchable directed/nondirected allylic substitution.

Authors:  Bernhard Breit; Peter Demel; Christopher Studte
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-19       Impact factor: 15.336

2.  Highly stereoselective anti SN2' substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents.

Authors:  Nicole Harrington-Frost; Helena Leuser; M Isabel Calaza; Florian F Kneisel; Paul Knochel
Journal:  Org Lett       Date:  2003-06-12       Impact factor: 6.005

3.  Cu-catalyzed asymmetric allylic alkylations of aromatic and aliphatic phosphates with alkylzinc reagents. An effective method for enantioselective synthesis of tertiary and quaternary carbons.

Authors:  Monica A Kacprzynski; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2004-09-01       Impact factor: 15.419

4.  Zirconium-mediated coupling reactions of amines and enol or allyl ethers: synthesis of allyl- and homoallylamines.

Authors:  José Barluenga; Félix Rodríguez; Lucía Alvarez-Rodrigo; José M Zapico; Francisco J Fañanás
Journal:  Chemistry       Date:  2004-01-05       Impact factor: 5.236

5.  Epoxide-opening and group-transfer reactions mediated by monomeric zirconium imido complexes.

Authors:  Suzanne A Blum; Patrick J Walsh; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2003-11-26       Impact factor: 15.419
  5 in total
  4 in total

1.  Regio- and stereospecific formation of protected allylic alcohols via zirconium-mediated S(N)2' substitution of allylic chlorides.

Authors:  Richard J Fox; Gojko Lalic; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2007-10-31       Impact factor: 15.419

2.  Neutral and Cationic Alkyl Tantalum Imido Complexes: Synthesis and Migratory Insertion Reactions.

Authors:  Laura L Anderson; Joseph A R Schmidt; John Arnold; Robert G Bergman
Journal:  Organometallics       Date:  2006-07-03       Impact factor: 3.876

3.  Scope and mechanism of formal S(N)2' substitution reactions of a monomeric imidozirconium complex with allylic electrophiles.

Authors:  Gojko Lalic; Jamin L Krinsky; Robert G Bergman
Journal:  J Am Chem Soc       Date:  2008-03-08       Impact factor: 15.419

4.  Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms.

Authors:  Guogang Deng; Shengzu Duan; Jing Wang; Zhuo Chen; Tongqi Liu; Wen Chen; Hongbin Zhang; Xiaodong Yang; Patrick J Walsh
Journal:  Nat Commun       Date:  2021-06-23       Impact factor: 14.919
  4 in total

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