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

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)3043-3052
Number of pages10
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number20
DOIs
Publication statusPublished - 1997 Oct 21

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Influence of a 2-fluoro substituent on diastereoselectivity in the 1,3-dipolar cycloadditions of nitrones'. Together they form a unique fingerprint.

Cite this