118263-73-3Relevant academic research and scientific papers
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
Mangelinckx, Sven,Nural, Yahya,Dondas, H. Ali,Denolf, Bram,Sillanp??, Reijo,De Kimpe, Norbert
experimental part, p. 4115 - 4124 (2010/07/05)
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.
SYNTHESIS OF 6-ARYL-4-HYDROXYPIPERIDIN-2-ONES AND A POSSIBLE APPLICATION TO THE SYNTHESIS OF A NOVEL HMG-CoA REDUCTASE INHIBITOR
Ashton, Michael J.,Hills, Susan J.,Newton, Christopher G.,Taylor, John B.,Tondu, Sylvie C. D.
, p. 1015 - 1035 (2007/10/02)
A series of 6-aryl-4-hydroxypiperidin-2-ones (11a-11g) were synthesised with the key step being a Dieckmann cyclisation of the appropriate methyl 3-(ethoxycarbonylacetylamino)-3-(substituted) propionate (8a-8g) and this new synthetic route was successfully applied to the synthesis of 4-hydroxy-6-(2-phenylethyl)piperidin-2-one (11h).The application of this strategy to the synthesis of the putative HMG-CoA reductase inhibitor 6--4-hydroxypiperidin-2-one (11i) was attempted, but failed during the Dieckmann cyclisation of methyl 3-(ethoxycarbonylacetylamino)- 3-propionate (8i).An alternative synthesis of a 1:1 diastereomeric mixture of (11i) was achieved by the reductive cleavage of the isoxazoline (24) with Raney nickel.The mixture of diastereoisomers (11i) was inactive in-vitro and in-vivo (rat) against HMG-CoA reductase
