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A novel oxidative ring-opening reaction of isoxazolidines: syntheses of β-amino ketones and β-amino acid esters from secondary amines

✍ Scribed by Shun-Ichi Murahashi; Yoichi Kodera; Tatsuhide Hosomi

Publisher: Elsevier Science
Year: 1988
Tongue: French
Weight: 203 KB
Volume: 29
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)82237-6

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✦ Synopsis

A novel oxidative ring-opening reaction of isoxazolidines upon treatment with an electrophile and subsequently with a base gives B-amino ketones and B-amino acid esters highly efficiently. Dipolar cycloaddition of nitrones with alkenes is an efficient method for the simultaneous formation of a carbon-carbon bond and a carbon-oxygen bond, and this strategy has been extensively exploited in the synthesis of various important synthetic key intermediates, such as B-amino aldehydes' and homoallylamines,' and natural products such as amino sugars and alkaloids. 3 We wish to report that isoxazolidines 3 can be converted into either B-amino . ketones 4 or B-amino acid esters 5 by novel oxidative ring-opening reactions.

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