PdCl2/CuCl2-catalysed chlorocyclisation of sugar-derived aminoalkenitols in the synthesis of new iminohexitols

The total synthesis of two novel l-ido and l-altro configured 6-chloro-1,5,6-trideoxyiminohexitols featuring a highly diastereoselective Pd(II)/CuCl2-catalysed chlorocyclisation of sugar-derived aminoalkenitols has been accomplished. The requisite substrates were, in turn, prepared from chiral pool materials starting from the cheap and commercially available methyl-α-d-gluco- and methyl-α-d-galactopyranoside.