Stereocontrolled conversion of some optically active (4S,5R)-dihydroisoxazoles into acyclic 3-acetamido-1,2-diols |
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Authors: | Jamie F BickleyStanley M Roberts Ye RunhuiJohn Skidmore Corina B Smith |
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Institution: | Department of Chemistry, Liverpool University, Liverpool L69 7ZD, UK |
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Abstract: | 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 α-amino acid derivatives 10a and 10b. |
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Keywords: | dihydroisoxazole amino-diols |
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