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  • Title: Highly stereoselective and scalable synthesis of trans-fused octahydrocyclohepta[b]pyrrol-4(1H)-ones via the aza-Cope-Mannich rearrangement in racemic and enantiopure forms.
    Author: Belov DS, Lukyanenko ER, Kurkin AV, Yurovskaya MA.
    Journal: J Org Chem; 2012 Nov 16; 77(22):10125-34. PubMed ID: 23113580.
    Abstract:
    We have developed an efficient and stereoselective route to trans-fused octahydrocyclohepta[b]pyrrol-4(1H)-ones. The key features of our synthesis include the regioselective epoxide ring-opening of alkynyl oxiranes and a stereoselective aza-Cope-Mannich reaction. The target compounds were prepared in 3-6 steps from commercially available starting materials (61-75% overall yield) with minimal chromatographic purification. We have devised an stereoselective route to target compounds using Shi epoxidation or (R)-1-phenylethylamine as a source of chirality.
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