Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines

Seiki Saito, Teruhiko Ishikawa, Toshio Moriwake

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

Intramolecular cycloaddition reactions of C5- chain acyclic alkenyl nitrones such as N-[(2S,3S)-2,3-bis-(tert-butyldimethylsiloxy)-4-pentenylidene]benzylamine N-oxide and its C(5)-substituted derivatives lead to fused isoxazolidines (bicyclo[3.2.0] framework) with very high diastereomeric excess. These isoxazolidines can readily be converted to optically active tetrasubstituted cyclobutylamines.

Original languageEnglish
Pages (from-to)4375-4377
Number of pages3
JournalJournal of Organic Chemistry
Volume59
Issue number16
DOIs
Publication statusPublished - Aug 1 1994

ASJC Scopus subject areas

  • Organic Chemistry

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