Literature DB >> 24823870

Enantioselective cycloisomerization of 1,6-enynes to bicyclo[3.1.0]hexanes catalyzed by rhodium and benzoic acid.

Koji Masutomi1, Keiichi Noguchi, Ken Tanaka.   

Abstract

It has been established that a cationic Rh(I)/(S)-Segphos or (S)-DTBM-Segphos complex and benzoic acid catalyze the enantioselective cycloisomerization of 1,6-enynes, possessing carbonyl groups at the enyne linkage, to 2-alkylidenebicyclo[3.1.0]hexanes. The present cycloisomerization may involve site selective γ-hydrogen elimination. The one-pot enantioselective cycloisomerization and lactonization of 1,6-enynes, leading to bicyclic lactones, has also been accomplished.

Entities:  

Year:  2014        PMID： 24823870     DOI： 10.1021/ja504048u

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


  4 in total

1.  Divergent reaction pathways in gold-catalyzed cycloisomerization of 1,5-enynes containing a cyclopropane ring: dramatic ortho substituent and temperature effects.

Authors:  Gen-Qiang Chen; Wei Fang; Yin Wei; Xiang-Ying Tang; Min Shi
Journal:  Chem Sci       Date:  2016-03-04       Impact factor: 9.825

2.  Synthesis of bridged tricyclo[5.2.1.01,5]decanes via nickel-catalyzed asymmetric domino cyclization of enynones.

Authors:  Jiachang Chen; Yiming Wang; Zhengtian Ding; Wangqing Kong
Journal:  Nat Commun       Date:  2020-04-20       Impact factor: 14.919

3.  Asymmetric intramolecular α-cyclopropanation of aldehydes using a donor/acceptor carbene mimetic.

Authors:  Chaosheng Luo; Zhen Wang; Yong Huang
Journal:  Nat Commun       Date:  2015-12-08       Impact factor: 14.919

4.  Synthesis of bicyclo[3.1.0]hexanes by (3 + 2) annulation of cyclopropenes with aminocyclopropanes.

Authors:  Bastian Muriel; Alec Gagnebin; Jerome Waser
Journal:  Chem Sci       Date:  2019-10-08       Impact factor: 9.825
  4 in total

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