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Heterogeneous Dipeptide‐Catalyzed α‐Amination of Aldehydes in a Continuous‐Flow Reactor: Effect of Residence Time on Enantioselectivity
Author(s) -
Ötvös Sándor B.,
Szloszár Aliz,
Mándity István M.,
Fülöp Ferenc
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500375
Subject(s) - chemistry , dipeptide , amination , catalysis , flow chemistry , residence time (fluid dynamics) , enantioselective synthesis , selectivity , continuous flow , combinatorial chemistry , electrophilic amination , organic chemistry , peptide , biochemical engineering , biochemistry , geotechnical engineering , engineering
A solid‐supported dipeptide‐catalyzed continuous‐flow process was developed for the direct enantioselective α‐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 α‐hydrazino alcohols were achieved with excellent ee s. 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.