Khan, Faiz Ahmed ; Upadhyay, Sarasij K. (2011) An efficient synthesis of a cyclopentannulated pyrrolidine derivative Synthesis, 2011 (15). pp. 2423-2430. ISSN 0039-7881
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Official URL: https://www.thieme-connect.com/ejournals/abstract/...
Related URL: http://dx.doi.org/10.1055/s-0030-1260114
Abstract
A racemic cyclopentannulated pyrrolidine derivative was synthesized utilizing ruthenium oxidation and borane reduction as the key steps. Ruthenium oxidation reaction of the 1,2-dibromoalkene moiety in an N-Boc-protected tetrabromonorbornyl derivative afforded a tricyclic α-hydroxy ketone, which on alkaline hydrogen peroxide cleavage furnished a bicyclic lactam in excellent yield. Borane reduction of the N-Boc-protected bicyclic lactam gave an unexpected product as a single diastereomer resulting from the reduction of not only the lactam and ester moieties but also the ketal to the corresponding methyl ether. A plausible mechanism involving an oxocarbenium ion is discussed.
Item Type: | Article |
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Source: | Copyright of this article belongs to Thieme Medical Publishers. |
Keywords: | Bicyclic Pyrrolidine; Ruthenium Oxidation; Borane Reduction; Diels-Alder Cycloaddition; Hydrodehalogenation |
ID Code: | 80347 |
Deposited On: | 31 Jan 2012 14:30 |
Last Modified: | 31 Jan 2012 14:30 |
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