Literature DB >> 22864054

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

Renhe Liu1, Min Zhang, Gabrielle Winston-McPherson, Weiping Tang.   

Abstract

Regioselective ring expansion of alkynyl cyclopropanes to highly substituted cyclobutenes was developed. The reaction involves a copper-catalyzed cycloaddition of an alkyne with an arylsulfonyl azide and a silver-catalyzed carbene formation followed by ring expansion of a cyclopropyl carbene intermediate.

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Year:  2012        PMID： 22864054      PMCID： PMC3717254          DOI： 10.1039/c2cc34609e

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  24 in total

1.  Recent Advances in Asymmetric Catalytic Metal Carbene Transformations.

Authors:  Michael P. Doyle; David C. Forbes
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Enantiomerically pure cyclobutane derivatives and their use in organic synthesis.

Authors:  Edward Lee-Ruff; Gabriela Mladenova
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3.  Gold-catalyzed oxidative ring expansions and ring cleavages of alkynylcyclopropanes by intermolecular reactions oxidized by diphenylsulfoxide.

Authors:  Chia-Wen Li; Kamalkishore Pati; Guan-You Lin; Shariar Md Abu Sohel; Hsiao-Hua Hung; Rai-Shung Liu
Journal:  Angew Chem Int Ed Engl       Date:  2010-12-17       Impact factor: 15.336

4.  Transition metal chemistry of cyclopropenes and cyclopropanes.

Authors:  Michael Rubin; Marina Rubina; Vladimir Gevorgyan
Journal:  Chem Rev       Date:  2007-07       Impact factor: 60.622

5.  Synthesis of cyclobutenes by highly selective transition-metal-catalyzed ring expansion of cyclopropanes.

Authors:  Huadong Xu; Wen Zhang; Dongxu Shu; Jenny B Werness; Weiping Tang
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 6.  Bioactive cyclobutane-containing alkaloids.

Authors:  Valery M Dembitsky
Journal:  J Nat Med       Date:  2007-09-05       Impact factor: 2.343

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

Authors:  Kazato Inanaga; Kiyosei Takasu; Masataka Ihara
Journal:  J Am Chem Soc       Date:  2005-03-23       Impact factor: 15.419

8.  Gold(I)-catalyzed intermolecular [2+2] cycloaddition of alkynes with alkenes.

Authors:  Verónica López-Carrillo; Antonio M Echavarren
Journal:  J Am Chem Soc       Date:  2010-07-14       Impact factor: 15.419

9.  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

Review 10.  Application of donor/acceptor-carbenoids to the synthesis of natural products.

Authors:  Huw M L Davies; Justin R Denton
Journal:  Chem Soc Rev       Date:  2009-09-30       Impact factor: 54.564
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  6 in total

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2.  Catalytic asymmetric transannulation of NH-1,2,3-triazoles with olefins.

Authors:  Sen Wai Kwok; Li Zhang; Neil P Grimster; Valery V Fokin
Journal:  Angew Chem Int Ed Engl       Date:  2014-03-24       Impact factor: 15.336

3.  Stereoselective 1,3-insertions of rhodium(II) azavinyl carbenes.

Authors:  Stepan Chuprakov; Brady T Worrell; Nicklas Selander; Rakesh K Sit; Valery V Fokin
Journal:  J Am Chem Soc       Date:  2013-12-17       Impact factor: 15.419

4.  Generation of rhodium(I) carbenes from ynamides and their reactions with alkynes and alkenes.

Authors:  Renhe Liu; Gabrielle N Winston-McPherson; Zhong-Yue Yang; Xin Zhou; Wangze Song; Ilia A Guzei; Xiufang Xu; Weiping Tang
Journal:  J Am Chem Soc       Date:  2013-05-23       Impact factor: 15.419

5.  Cu-Catalyzed Transannulation Reaction of Pyridotriazoles with Terminal Alkynes under Aerobic Conditions: Efficient Synthesis of Indolizines.

Authors:  V Helan; A V Gulevich; V Gevorgyan
Journal:  Chem Sci       Date:  2015-03       Impact factor: 9.825

6.  Tandem 1,2-sulfur migration and (aza)-Diels-Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes.

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Journal:  Chem Sci       Date:  2015-07-10       Impact factor: 9.825
  6 in total

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