Heterogeneous Dipeptide-Catalyzed a-Amination of Aldehydes in a Continuous-Flow Reactor: Effect of Residence Time on Enantioselectivity

Ötvös, Sándor Balázs and Szloszar, Aliz and Mándity, István and Fülöp, Ferenc (2015) Heterogeneous Dipeptide-Catalyzed a-Amination of Aldehydes in a Continuous-Flow Reactor: Effect of Residence Time on Enantioselectivity. Advanced Synthesis and Catalysis, 357 (16-17). pp. 3671-3680. ISSN 1615-4150

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Abstract

A solid-supported dipeptide-catalyzed continuous-flow process was developed for the direct enantioselective a-amination of aldehydes with dibenzyl azodicarboxylate as the electrophilic nitrogen source. With residence time control as an efficient tool for the fine-tuning of the enantioselectivity, synthetically useful a-hydrazino alcohols were achieved with excellent ees. The packed-bed system proved to be highly robust: no decrease in catalyst activity or selectivity was detected throughout 20 h of continuous-flow operation.

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