Literature DB >> 26551769

Stereoselective Synthesis of β-Lactam-triflones under Catalyst-Free Conditions.

Zhongyan Huang1, Chen Wang1, Etsuko Tokunaga1, Yuji Sumii1, Norio Shibata1.   

Abstract

The first example of the synthesis of β-lactam-triflones is described. Treatment of 2-diazo-1-aryl-2-(trifluoromethylsulfonyl)ethanones 1c-f with imines 2 under catalyst-free heating conditions provides pharmaceutically attractive multisubstituted β-lactam-triflones 3 in good to high yields with regio- and diastereoselectivities. A successive Wolff rearrangement and Staudinger [2 + 2] cycloaddition reaction are key elements for the success of this transformation.

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Year:  2015        PMID： 26551769     DOI： 10.1021/acs.orglett.5b02827

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


  5 in total

1.  Synthesis of Aryl Triflones through the Trifluoromethanesulfonylation of Benzynes.

Authors:  Yuji Sumii; Yutaka Sugita; Etsuko Tokunaga; Norio Shibata
Journal:  ChemistryOpen       Date:  2018-02-27       Impact factor: 2.911

2.  Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety via a double decarboxylative formal ring-expansion process under palladium catalysis.

Authors:  Pulakesh Das; Satoshi Gondo; Punna Nagender; Hiroto Uno; Etsuko Tokunaga; Norio Shibata
Journal:  Chem Sci       Date:  2018-02-23       Impact factor: 9.825

3.  Catalytic Enantioselective Entry to Triflones Featuring a Quaternary Stereocenter.

Authors:  Francesca Franco; Sara Meninno; Jacob Overgaard; Sergio Rossi; Maurizio Benaglia; Alessandra Lattanzi
Journal:  Org Lett       Date:  2022-06-10       Impact factor: 6.072

4.  2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions.

Authors:  Zhongyan Huang; Kenta Okuyama; Chen Wang; Etsuko Tokunaga; Xiaorui Li; Norio Shibata
Journal:  ChemistryOpen       Date:  2016-01-28       Impact factor: 2.911

5.  Structure-Activity Relationship Studies of β-Lactam-azide Analogues as Orally Active Antitumor Agents Targeting the Tubulin Colchicine Site.

Authors:  Dong-Jun Fu; Ling Fu; Ying-Chao Liu; Jun-Wei Wang; Yu-Qing Wang; Bing-Kai Han; Xiao-Rui Li; Chuang Zhang; Feng Li; Jian Song; Bing Zhao; Ruo-Wang Mao; Ruo-Han Zhao; Sai-Yang Zhang; Li Zhang; Yan-Bing Zhang; Hong-Min Liu
Journal:  Sci Rep       Date:  2017-10-06       Impact factor: 4.379
  5 in total

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