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

• DOI: 10.1016/j.tet.2006.06.078
• Publication Date: 2006-07-13T12:18:54Z
• Authors: Peter Szolcsányi; Tibor Gracza
• Keywords: 01 natural sciences; 0104 chemical sciences

Abstract 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.