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Formation of α‐Amino Ketones: Addition of Acylzirconocene Chlorides to Imines Catalyzed by Yb(OTf) 3 /TmsOTf and Brønsted Acids and Three‐Component Reactions of Acylzirconocene Chlorides, Aldehydes, and Amines
Author(s) -
Kakuuchi Akito,
Taguchi Takeo,
Hanzawa Yuji
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200301)2003:1<116::aid-ejoc116>3.0.co;2-3
Subject(s) - chemistry , catalysis , ketone , brønsted–lowry acid–base theory , organic chemistry , medicinal chemistry
A direct preparation of α‐amino ketone derivatives through treatment of acylzirconocene chlorides with N ‐benzylideneaniline derivatives, in which acylzirconocene chlorides react as “unmasked” acyl anion donors, was carried out under Yb(OTf) 3 /TMSOTf‐catalyzed conditions. The same reactions were also carried out with the use of Brønsted acids as catalyst in place of Yb(OTf) 3 /TMSOTf. The operationally simple three‐component reaction with aldehydes, anilines, and acylzirconocene chlorides affords α‐amino ketone derivatives essentially in the absence of a catalyst. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)