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

DOI: 10.1021/jo00095a008

Source and publish data:

Journal of Organic Chemistry p. 4375 - 4377 (1994)

Update date:2022-07-30

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Authors:

Saito, Seiki

Ishikawa, Teruhiko

Moriwake, Toshio

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Article abstract of DOI:10.1021/jo00095a008

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.

Full text of DOI:10.1021/jo00095a008

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