Literature DB >> 19199306

Rhodium(I)-catalyzed intramolecular carbonylative [2+2+1] cycloaddition of bis(allene)s: bicyclo[6.3.0]undecadienones and bicyclo[5.3.0]decadienones.

Fuyuhiko Inagaki1, Syu Narita, Takuma Hasegawa, Shinji Kitagaki, Chisato Mukai.   

Abstract

No templates needed: The title reaction makes it easy to construct the bicyclo[6.3.0]undecadienone framework in high yields (see scheme). A template effect is not required to achieve this ring-closing reaction efficiently. The present method can be applied to the construction of bicyclo[5.3.0] and bicyclo[4.3.0] ring systems. Ts = p-toluenesulfonyl.

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Year:  2009        PMID: 19199306     DOI: 10.1002/anie.200806029

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  2 in total

1.  Rh(I)-catalyzed intramolecular [2 + 2 + 1] cycloaddition of allenenes: Construction of bicyclo[4.3.0]nonenones with an angular methyl group and tricyclo[6.4.0.0]dodecenone.

Authors:  Fuyuhiko Inagaki; Naoya Itoh; Yujiro Hayashi; Yumi Matsui; Chisato Mukai
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

2.  Reactivity and chemoselectivity of allenes in Rh(I)-catalyzed intermolecular (5 + 2) cycloadditions with vinylcyclopropanes: allene-mediated rhodacycle formation can poison Rh(I)-catalyzed cycloadditions.

Authors:  Xin Hong; Matthew C Stevens; Peng Liu; Paul A Wender; K N Houk
Journal:  J Am Chem Soc       Date:  2014-11-24       Impact factor: 15.419

  2 in total

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