Enantioselective Electrophilic Amination of α-Cyanothioacetates with Azodicarboxylates Catalyzed by an Axially Chiral Guanidine Base

Enantioselective Electrophilic Amination of α-Cyanothioacetates with Azodicarboxylates Catalyzed by an Axially Chiral Guanidine Base

An enantioselective electrophilic amination of α‐substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Brønsted base catalyst. The corresponding product, having a quaternary stereogenic center at the α‐carbon atom, is formed in excellent en...

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Veröffentlicht in:Advanced synthesis & catalysis 2009-11, Vol.351 (17), p.2817-2821
Hauptverfasser: Terada, Masahiro, Tsushima, Daisuke, Nakano, Megumi
Format: Artikel
Sprache:eng
Schlagworte:
amination
amino acids
asymmetric catalysis
organocatalysis
quaternary stereocenters
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Zusammenfassung:An enantioselective electrophilic amination of α‐substituted cyanothioacetates with azodicarboxylate is demonstrated using an axially chiral guanidine as a chiral Brønsted base catalyst. The corresponding product, having a quaternary stereogenic center at the α‐carbon atom, is formed in excellent enantioselectivity.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200900594