Premium
Organocatalyzed Enantioselective Synthesis of 2‐Amino‐4 H ‐chromene Derivatives
Author(s) -
Ramireddy Naresh,
Abbaraju Santhi,
Ding Derong,
Arman Hadi,
Zhao John C.G.
Publication year - 2017
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.2641
Subject(s) - chemistry , malononitrile , enantioselective synthesis , bifunctional , cinchona , tandem , organic chemistry , organocatalysis , catalysis , amino acid , michael reaction , medicinal chemistry , materials science , composite material , biochemistry
Optically active 2‐amino‐5‐oxo‐5,6,7,8‐tetrahydro‐4 H ‐chromene‐3‐carboxylates, 2‐amino‐5‐oxo‐5,6,7,8‐tetrahydro‐4 H ‐chromene‐3‐carbonitriles, and 2‐amino‐8‐oxo‐5,6,7,8‐tetrahydro‐4 H ‐chromene‐3‐carbonitriles were synthesized. Using cinchona alkaloid‐derived bifunctional catalysts, the corresponding 2‐amino‐4 H ‐chromene derivatives were obtained in high yields and moderate to high ee values (up to 82% ee) from the tandem Michael addition–cyclization reaction between 1,3‐cyclohexanediones or 1,2‐cyclohexanediones and ( E )‐3‐aryl‐2‐cyanoacrylate or alkylidene malononitrile derivatives.