Literature DB >> 15771480

A practical catalytic method for preparing highly substituted cyclobutanes and cyclobutenes.

Kazato Inanaga1, Kiyosei Takasu, Masataka Ihara.   

Abstract

Tf2NH, an organic acid, efficiently catalyzes (2 + 2) cycloaddition reactions of silyl enol ethers with acrylates or propiolate. The process affords highly substituted cyclobutanes in high yield with high stereoselectivity under practical and environmentally benign conditions. Application for the formation of terpene skeletons and multigram synthesis of four-membered carbocycles were demonstrated.

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Year:  2005        PMID： 15771480     DOI： 10.1021/ja042661s

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


  6 in total

1.  A strategy toward the synthesis of C13-oxidized cembrenolides.

Authors:  Alec Saitman; Steven D E Sullivan; Emmanuel A Theodorakis
Journal:  Tetrahedron Lett       Date:  2013-03-20       Impact factor: 2.415

2.  Stereoselective preparation of cyclobutanes with four different substituents: total synthesis and structural revision of pipercyclobutanamide A and piperchabamide G.

Authors:  Renhe Liu; Min Zhang; Thomas P Wyche; Gabrielle N Winston-McPherson; Tim S Bugni; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2012-06-19       Impact factor: 15.336

3.  Ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes via a N-sulfonyl-1,2,3-triazole intermediate.

Authors:  Renhe Liu; Min Zhang; Gabrielle Winston-McPherson; Weiping Tang
Journal:  Chem Commun (Camb)       Date:  2012-08-03       Impact factor: 6.222

4.  Facile isomerization of silyl enol ethers catalyzed by triflic imide and its application to one-pot isomerization-(2 + 2) cycloaddition.

Authors:  Kazato Inanaga; Yu Ogawa; Yuuki Nagamoto; Akihiro Daigaku; Hidetoshi Tokuyama; Yoshiji Takemoto; Kiyosei Takasu
Journal:  Beilstein J Org Chem       Date:  2012-04-27       Impact factor: 2.883

5.  Cyclobutene vs 1,3-Diene Formation in the Gold-Catalyzed Reaction of Alkynes with Alkenes: The Complete Mechanistic Picture.

Authors:  M Elena de Orbe; Laura Amenós; Mariia S Kirillova; Yahui Wang; Verónica López-Carrillo; Feliu Maseras; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2017-07-25       Impact factor: 15.419

6.  Retracted Article: An efficient one pot three-component synthesis of 2,4,6-triarylpyridines using triflimide as a metal-free catalyst under solvent-free conditions.

Authors:  Hongshe Wang; Weixing Zhao; Juan Du; Fenyan Wei; Qi Chen; Xiaomei Wang
Journal:  RSC Adv       Date:  2019-02-12       Impact factor: 3.361
  6 in total

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