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Organocatalytic α‐Addition of Isocyanides to Aldehydes
Author(s) -
Yamada Takeshi,
Hirose Tomoyasu,
Ōmura Satoshi,
Sunazuka Toshiaki
Publication year - 2015
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/ejoc.201403313
Subject(s) - chemistry , catalysis , inert gas , solvent , organic chemistry , organocatalysis , benzene , aldehyde , combinatorial chemistry , enantioselective synthesis
α‐Hydroxyamide is an important chemical component widely observed in biologically active natural products. One of the most direct methods to access a α‐hydroxyamide is the Passerini‐type reaction. However, this catalytic process was limited. Herein, we report the first examples of 3,5,6‐trifluoro‐2‐pyridone‐catalyzed α‐addition of isocyanides to aldehydes, in the presence of water in benzene, to provide α‐hydroxyamides. Various aldehydes and isocyanides performed well in this reaction to provide the α‐hydroxyamides. Even highly constrained substrates were well tolerated. The reaction is not restricted by requirements of either inconvenient temperature control, inert atmosphere or dry solvent. The new catalytic reaction may open the way to development of asymmetric organocatalytic α‐addition of isocyanides.