In this communication we will show the various strategies applied to obtain 4,5-dihydroisoxazoles 5-substituted with a ketonic group and in particular on 5-acetyl-Δ2-isoxazolines bearing in position 3 a methyl or a carbethoxy group in enantiomerically pure form. Moreover it will be reported the condensation reaction between the enantiopure isoxazolines and Schöllkopf reagent enolate, that has occured with a good diastereoselectivity, providing only two of the four possible adducts with 70:30 d.r. Finally the best hydrolysis condition of the adducts, that has provided β-Δ2-isoxazolinyl-threonines,will be illustrated.
Stereoselective synthesis of beta-Δ2-isoxazolinyl-threonines / G. Cremonesi, P. Dalla Croce, M. Gallanti, C. La Rosa. ((Intervento presentato al 12. convegno RSC-SCI Joint Meeting on Heterocyclic Chemistry tenutosi a Brighton nel 2010.
Stereoselective synthesis of beta-Δ2-isoxazolinyl-threonines
G. CremonesiPrimo
;P. Dalla CroceSecondo
;M. GallantiPenultimo
;C. La RosaUltimo
2010
Abstract
In this communication we will show the various strategies applied to obtain 4,5-dihydroisoxazoles 5-substituted with a ketonic group and in particular on 5-acetyl-Δ2-isoxazolines bearing in position 3 a methyl or a carbethoxy group in enantiomerically pure form. Moreover it will be reported the condensation reaction between the enantiopure isoxazolines and Schöllkopf reagent enolate, that has occured with a good diastereoselectivity, providing only two of the four possible adducts with 70:30 d.r. Finally the best hydrolysis condition of the adducts, that has provided β-Δ2-isoxazolinyl-threonines,will be illustrated.
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