Literature DB >> 29504644

Catalytic [1,3] O-to-C Rearrangement: Rapid Access to Bridged Bicyclic Systems.

Jiantao Zhang1, Zhehui Liao1, Lianfen Chen1, Huanfeng Jiang1, Shifa Zhu1.   

Abstract

A catalytic [1,3] O-to-C rearrangement from enyne-ethers was developed for the rapid synthesis of diverse bridged bicyclic systems. In this reaction, a vinyl oxonium intermediate, generated in situ from enyne-ether, was the precursor for the [1,3] O-to-C rearrangement. This versatile protocol represents the first example of catalytic [1,3] O-to-C rearrangement based on ring-expansion strategy, enabling efficient access to bridged bicyclic scaffolds.
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  [1,3]-rearrangement; [3,3]-rearrangement; bridged bicycles; gold; ring-expansion reactions

Year:  2018        PMID: 29504644     DOI: 10.1002/chem.201801062

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  2 in total

1.  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

2.  Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.

Authors:  Lifeng Wang; Pengfei Zhou; Qianchi Lin; Shunxi Dong; Xiaohua Liu; Xiaoming Feng
Journal:  Chem Sci       Date:  2020-09-07       Impact factor: 9.825

  2 in total

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