One-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole 2-oxides.
[structure: see text]. A new methodology for the one-pot direct conversion of 2,3-epoxy alcohols into enantiomerically pure 4-hydroxy-4,5-dihydroisoxazole 2-oxides 1 has been found. The reaction works at room temperature and can be run at the 5-10 g scale. The mixture of 4,5-cis and 4,5-trans isomers obtained can be separated as such or as the bis-TDS ethers. A preliminary example of reductive cleavage of 1 to the corresponding amino polyol is also reported.
Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Viale del Risorgimento, 4 - I-40136 Bologna, Italy.
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E
Marotta
L M
LM
Micheloni
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N
Scardovi
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P
Righi
D000438:Alcohols / Q000138:chemical synthesis*; D017607:Aluminum Compounds; D004852:Epoxy Compounds / Q000737:chemistry*; D007202:Indicators and Reagents; D007555:Isoxazoles / Q000138:chemical synthesis*; D018020:Lithium Compounds; D008968:Molecular Conformation; D013237:Stereoisomerism
D000438:Alcohols; D017607:Aluminum Compounds; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D007555:Isoxazoles; D018020:Lithium Compounds; C042073:lithium aluminum hydride