H. Hioki et al., INTRAMOLECULAR AMIDOALKYLATION OF CHIRAL IMINES AND IMINIUM IONS - STEREOSELECTIVE SYNTHESIS OF ANTI-1,2-AMINOALCOHOL AND ANTI-1,3-AMINOALCOHOL, Tetrahedron letters, 36(13), 1995, pp. 2289-2292
When treated with Lewis acids, 2- or 3-vinyl- or -phenylsiloxyaminoace
tals generated the corresponding imines or iminium ions which in turn
underwent smooth intramolecular amidoalkylation to afford anti-1,2- or
-1,3-aminoalcohol derivatives in very high chemical yields and excell
ent diastereomeric ratios. Applying the reaction, Z-allo-L-threonine a
nd (+/-)-N-ethoxycarbonyl-anti-gamma-hydroxynorvaline were successfull
y synthesized.