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Synfacts 2013; 9(1): 0096
DOI: 10.1055/s-0032-1317897
DOI: 10.1055/s-0032-1317897
Organo- and Biocatalysis
Thiourea-Catalyzed Asymmetric Cyanation of N-Boc Ketimines
Liu Y.-L, Zhou J * East China Normal University, Shanghai, China
Organocatalytic Asymmetric Cyanation of Isatin Derived N-Boc Ketoimines.
Chem. Commun. 2013;
DOI: 10.1039/c2cc36665g
Organocatalytic Asymmetric Cyanation of Isatin Derived N-Boc Ketoimines.
Chem. Commun. 2013;
DOI: 10.1039/c2cc36665g
Further Information
Publication History
Publication Date:
17 December 2012 (online)
Significance
The first catalytic asymmetric cyanation of isatin-derived N-Boc ketimines has been reported by Zhou and co-worker. Wide substrate scope and excellent enantioselectivities were obtained. A tandem aza-Wittig–Strecker reaction has also been reported, which was applied to the total synthesis of spirohydantoin I.
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Comment
An aza-Wittig–Strecker reaction sequence has been reported, which offers a good methodology to develop a catalytic asymmetric reaction of N-Boc ketimines, generated in situ from the achiral ketones. The strategy has potential applications in other types of reactions, in which N-Boc imines are involved.
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