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

作者：Mangelinckx Sven; Nural Yahya; Dondas H Ali; Denolf Bram; Sillanpaa Reijo; De Kimpe Norbert^*

来源：Tetrahedron, 2010, 66(23): 4115-4124.

DOI：10.1016/j.tet.2010.03.113

• Cyclocarbamation
• 1,3-Oxazinan-2-ones
• 1,3-Aminoalcohols
• Piperidine-2,4-diones

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.

• 出版日期2010-6-5