Diastereoselective synthesis of 6-functionalized 4-aryl-1,3-oxazinan-2-ones and their application in the synthesis of 3-aryl-1,3-aminoalcohols and 6-arylpiperidine-2,4-diones |
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Authors: | Sven Mangelinckx Yahya Nural Bram Denolf Norbert De Kimpe |
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Institution: | a Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000, Ghent, Belgium b Department of Basic Pharmaceutical Sciences, Faculty of Pharmacy, Mersin University, Yenisehir, Mersin, Turkey c Department of Chemistry, University of Jyväskylä, Fin-40351, Jyväskylä, Finland |
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Abstract: | Halocyclocarbamation of benzyl N-(1-phenyl-3-butenyl)carbamates afforded 6-functionalized 4-aryl-1,3-oxazinan-2-ones with moderate to excellent diastereoselectivity depending on the N-substituent. Importantly, in contrast to reported cyclocarbamations of homoallylic carbamates, which are generally trans-diastereoselective, cyclization of N-unsubstituted Cbz-protected homoallylamines led to cis-1,3-oxazinan-2-ones, predominantly. The use of N-benzylated and in situ prepared N-silylated derivatives resulted however in trans-selectivity. Transition states are proposed to explain the stereochemical influence of the N-substituent on the cyclocarbamations. The functionalized 1,3-oxazinan-2-ones could be further elaborated towards biologically or synthetically important 6-arylpiperidine-2,4-diones and 3-aryl-1,3-aminoalcohols. |
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Keywords: | Cyclocarbamation 1 3-Oxazinan-2-ones 1 3-Aminoalcohols Piperidine-2 4-diones |
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