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Stereocontrolled conversion of some optically active (4S,5R)-dihydroisoxazoles into acyclic 3-acetamido-1,2-diols

✍ Scribed by Jamie F Bickley; Stanley M Roberts; Ye Runhui; John Skidmore; Corina B Smith

Book ID: 104205505
Publisher: Elsevier Science
Year: 2003
Tongue: French
Weight: 130 KB
Volume: 59
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(03)00868-8

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✦ Synopsis

Optically active (4S,5R)-dihydroisoxazoles 5a -c (90 -91% ee) have been prepared by reaction of the epoxyketones 4a -c with hydroxylamine. Reduction of compounds 5a and 5b using lithium aluminium hydride took place exclusively from the Re face to give (1R,2S,3S)-1,3-disubstituted-3-aminopropane-1,2-diols 6a and 6b. These amino-diols were characterised by N-acetylation and the stereochemical sense of the hydride reduction was confirmed by conversion of amides 7a and 7b into a-amino acid derivatives 10a and 10b.

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