Vyavahare, Vinod P. ; Chattopadhyay, Subrata ; Puranik, Vedavati G. ; Dhavale, Dilip D. (2007) Rh(II)-catalyzed intramolecular N-H insertion of D-glucose-derived δ-amino α-diazo β-ketoester: synthesis of pyrrolidine iminosugars Synlett, 4 . 0559-0562. ISSN 0936-5214
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Official URL: https://www.thieme-connect.com/ejournals/abstract/...
Related URL: http://dx.doi.org/10.1055/s-2007-970743
Abstract
The rhodium acetate catalyzed reaction of D-glucose-derived δ-amino α-diazo β-ketoester allows a stereoselective β-facial intramolecular N-H insertion reaction that leads to formation of the bicyclic pyrrolidinone ring skeleton in high yield. The sugar- sub stituted pyrrolidinone thus obtained was elaborated to allow the synthesis of promising glycosidase inhibitors, namely, 2,5-dideoxy-2,5-imino-L-glycero-α-D- galactoheptitol and 2,5-dideoxy-2,5-imino-D-galactitol.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers. |
| Keywords: | Alkaloids; Azasugars; Carbohydrates; Pyrrolidines; Rhodium Carbenoid; N-H Insertion |
| ID Code: | 75337 |
| Deposited On: | 22 Dec 2011 13:12 |
| Last Modified: | 22 Dec 2011 13:12 |
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