Tetrahedron Asymmetry p. 2975 - 2987 (1997)
Update date:2022-08-29
Topics:
Battistini, Lucia
Zanardi, Franca
Rassu, Gloria
Spanu, Pietro
Pelosi, Giorgio
Gasparri Fava, Giovanna
Belicchi Ferrari, Marisa
Casiraghi, Giovanni
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.
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