Regio- and facial-selective effects of allylic heteroatoms in 1,3-dipolar cycloaddition of a nitrile oxide.

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概要

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• The 1,3-dipolar cycloaddition of nitrile oxides to 2-X-bicyclo[2.2.2]oct-5-enes (X=O, NMe, S, SO<SUB>2</SUB>) were investigated together with acyclic and alicyclic analogues. The regioselectivity in an <I>exo</I>-attack was controlled by the heteroatom present at an allylic position —a remote attack was predominant in the cases of O and SO<SUB>2</SUB> but a vicinal attack in those of NMe and S— and the results were rationalized from the electronic nature of the heteroatom, X. In an <I>endo</I>-attack, a remote attack was observed in every case and the dipole-dipole repulsion between X and the oxygen of the nitrile oxide was considered to be a predominant factor. The steric environment around the heteroatom controled the facial-selectivity.

• 公益社団法人 日本化学会の論文

著者

• Inouye Yoshinobu

  Department Of Chemistry The University Of Tsukuba

• Kakisawa Hiroshi

  Department Of Chemistry University Of Tsukuba

• Mitsuya Morihiro

  Department of Chemistry, University of Tsukuba

• Tokuhisa Kenji

  Department of Chemistry, University of Tsukuba

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