852612-03-4Relevant articles and documents
Regioselective cleavage of the bis-benzylidene acetal of D-mannitol under oxidative and reductive conditions: A new approach to C2-symmetric chiral ligands
Aravind, Appu,Mohanty, Subhendu K.,Pratap, T. Veerabhadra,Baskaran, Sundarababu
, p. 2965 - 2968 (2007/10/03)
A highly regioselective oxidative cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was carried out using NBS and the resultant product was readily converted to the C2-symmetric chiral ligand, (R,R)-3,4-dihydroxy-1,5- hexadiene. On the other hand, reductive cleavage of 1,3:4,6-di-O-benzylidene-d- mannitol was achieved in a highly regioselective manner using BF 3?OEt2 and Et3SiH to give a highly functionalized benzyl ether, which was converted to a synthetically useful C2-symmetric bis-amino alcohol derivative.