Literature DB >> 33844548

A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement.

Seo-Jung Han1,2, Marchello A Cavitt1, Brian M Stoltz1.   

Abstract

Eight-membered nitrogen-containing heterocycles were straightforwardly produced by a nickel-catalyzed cycloetherification and subsequent Claisen rearrangement of secondary and tertiary alcohols. In particular, a one-pot transformation was achieved with tertiary alcohols in moderate to good yields. This operationally simple reaction is tolerant of many functional groups and applicable to the synthesis of various medium-sized ring nitrogen-containing heterocycles.

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Year:  2021        PMID: 33844548      PMCID: PMC8846577          DOI: 10.1021/acs.orglett.1c00763

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


  3 in total

1.  Combined rhodium-catalyzed carbon-hydrogen activation and beta-carbon elimination to access eight-membered rings.

Authors:  Damien Crépin; James Dawick; Christophe Aïssa
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

2.  Nickel-Catalyzed Intramolecular C-O Bond Formation: Synthesis of Cyclic Enol Ethers.

Authors:  Seo-Jung Han; Ryohei Doi; Brian M Stoltz
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-09       Impact factor: 15.336

3.  Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.

Authors:  Bo Zhou; Ying-Qi Zhang; Kairui Zhang; Ming-Yang Yang; Yang-Bo Chen; You Li; Qian Peng; Shou-Fei Zhu; Qi-Lin Zhou; Long-Wu Ye
Journal:  Nat Commun       Date:  2019-07-19       Impact factor: 14.919

  3 in total
  1 in total

1.  Identifying the Imperative Role of Metal-Olefin Interactions in Catalytic C-O Reductive Elimination from Nickel(II).

Authors:  Trevor D Lohrey; Alexander Q Cusumano; William A Goddard; Brian M Stoltz
Journal:  ACS Catal       Date:  2021-08-02       Impact factor: 13.700

  1 in total

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