Regioselective cleavage of the bis-benzylidene acetal of d-mannitol under oxidative and reductive conditions: a new approach to C2-symmetric chiral ligands |
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Authors: | Appu Aravind |
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Institution: | Department of Chemistry, Indian Institute of Technology Madras, Chennai 600 036, India |
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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 a synthetically useful C2-symmetric bis-amino alcohol derivative. |
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Keywords: | Regioselective Oxidative cleavage Reductive cleavage C2-symmetric Chiral ligand |
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