Aravind, Appu ; Mohanty, Subhendu K. ; Pratap, Veerabhadra T. ; Baskaran, Sundarababu (2005) Regioselective cleavage of the bis-benzylidene acetal of d-mannitol under oxidative and reductive conditions: a new approach to C2-symmetric chiral ligands Tetrahedron Letters, 46 (17). pp. 2965-2968. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2005.03.038
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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Regioselective; Oxidative Cleavage; Reductive Cleavage; C2-symmetric; Chiral Ligand |
| ID Code: | 98550 |
| Deposited On: | 18 Sep 2014 11:05 |
| Last Modified: | 18 Sep 2014 11:06 |
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