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
Publication statusPublished - 1994

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Cycloaddition
Oxides
Derivatives
Controllers
nitrones
benzylamine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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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.",
author = "Seiki Saito and Teruhiko Ishikawa and Toshio Moriwake",
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pages = "4375--4377",
journal = "Journal of Organic Chemistry",
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AU - Ishikawa, Teruhiko

AU - Moriwake, Toshio

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