trans-β-Hydroxypipecolic acids of both L- and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively, starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acids.
Total synthesis of both enantiomers of trans-β-hydroxypipecolic acid / Battistini, L.; Zanardi, F.; Rassu, G.; Spanu, P.; Pelosi, G.; Gasparri Fava, G.; Belicchi Ferrari, M.; Casiraghi, G.. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 8:17(1997), pp. 2975-2987. [10.1016/S0957-4166(97)00344-3]
Total synthesis of both enantiomers of trans-β-hydroxypipecolic acid
Battistini L.;Zanardi F.;Pelosi G.;Belicchi Ferrari M.;Casiraghi G.
1997-01-01
Abstract
trans-β-Hydroxypipecolic acids of both L- and D-series, L-1 and D-1, have been straightforwardly prepared in 14% and 15% yields, respectively, starting from glyceraldehyde imines D-7 and L-7 as useful three-carbon chirons. The key feature of these parallel syntheses lies on the highly diastereoselective character of the initial coupling manoeuver between silyloxy furan TBSOF and imines 7, which ultimately accounts for the relative, and hence absolute configuration of the target pipecolic acids.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
