Influence of a 2-fluoro substituent on diastereoselectivity in the 1,3-dipolar cycloadditions of nitrones

Masataka Ihara, Yuko Tanaka, Nobuyuki Takahashi, Yuji Tokunaga, Keiichiro Fukumoto

研究成果: Article査読

16 被引用数 (Scopus)

抄録

It is clear that the role of 1,2-asymmetric induction on the 1,3-dipolar cycloaddition of nitrones is influenced by the presence of a fluorine atom at the C-2 position. 2-Fluoro nitrones, synthesized by three different methods, have been subjected to the intermolecular 1,3-dipolar cycloaddition with ethyl vinyl ether. The stereostructures of isoxazolidines formed were determined by their conversion into 2,7-dioxa-6-azabicyclo[3.2.1]octanes. The diastereoselectivity of 2-fluoro nitrones was the reverse of that of the corresponding 2-hydro nitrones. This fact supports that the conformation with relief from the dipole repulsion between the fluorine atom and the oxygen atom of the nitrone is a preferred one for 2-fluoro nitrones, while the corresponding 2-hydro nitrones adopt the conformation with the least 1,3-allylic strain.

本文言語English
ページ(範囲)3043-3052
ページ数10
ジャーナルJournal of the Chemical Society - Perkin Transactions 1
20
DOI
出版ステータスPublished - 1997 10 21

ASJC Scopus subject areas

  • 化学 (全般)

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