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

doi:10.1021/jo00095a008

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 journal › Article › peer-review

7 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 language	English
Pages (from-to)	4375-4377
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	59
Issue number	16
DOIs	https://doi.org/10.1021/jo00095a008
Publication status	Published - Aug 1 1994

ASJC Scopus subject areas

Organic Chemistry

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Role of a Protected Vicinal Diol Controller in Intramolecular [3 + 2] Cycloaddition Reactions of Chiral Acyclic Alkenyl Nitrones: Syntheses of Enantiomerically Pure Tetrasubstituted Cyclobutylamines. / Saito, Seiki; Ishikawa, Teruhiko; Moriwake, Toshio.
In: Journal of Organic Chemistry, Vol. 59, No. 16, 01.08.1994, p. 4375-4377.

Research output: Contribution to journal › Article › peer-review

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

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