Jadhav, Vrushali H. ; Bande, Omprakash P. ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2010) Synthesis of eight-membered iminocyclitols from D-glucose Tetrahedron, 66 (15). pp. 2830-2834. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/j.tet.2010.02.044
Abstract
The Baylis-Hillman reaction of 3-O-benzyl-α-D-xylo-pentodialdo-1,4-furanose 2 afforded a diastereomeric mixture of L-ido- and D-gluco-configurated α-methylene-β-hydroxy esters 3a and 3b, respectively, in 1:1 ratio. Conjugate addition of benzyl amine on 3a gave adduct 4a as a major product while, addition of benzyl amine to 3b gave only one diastereomer 4b. Reduction of ester functionality in 4a/4b, opening of 1,2-acetonide functionality followed by reductive amino-cyclization under hydrogenation condition afforded azocanes 1c/1d in good yield.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Baylis-hillman Reaction; Conjugate Addition; Iminosugars; Diastereoselectivity |
| ID Code: | 9733 |
| Deposited On: | 02 Nov 2010 10:49 |
| Last Modified: | 31 May 2011 11:48 |
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