Tetrahedron letters

Regioselective cleavage of the bis-benzylidene acetal of d-mannitol under oxidative and reductive conditions: a new approach to C 2-symmetric chiral ligands

A Aravind, SK Mohanty, TV Pratap, S Baskaran

Index: Aravind, Appu; Mohanty, Subhendu K.; Pratap, T. Veerabhadra; Baskaran, Sundarababu Tetrahedron Letters, 2005 , vol. 46, # 17 p. 2965 - 2968

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Citation Number: 11

Abstract

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 BF3· OEt2 and Et3SiH to give a highly functionalized benzyl ether, which was converted to ...