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

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.
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]
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11381/2884895
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