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DABCO‐Catalyzed the Synthesis of Densely Functionalized Cyclohexanones in a Benign Manner
Author(s) -
Hazeri Nourallah,
Lashkari Mojtaba,
Fatahpour Maryam,
Sheikhveisi Mahla
Publication year - 2020
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.12067
Subject(s) - dabco , stereocenter , chemistry , yield (engineering) , catalysis , reaction conditions , solvent , stereoselectivity , aryl , column chromatography , organic chemistry , combinatorial chemistry , enantioselective synthesis , materials science , alkyl , metallurgy
In this study, a robust DABCO‐catalyzed method has been reported for the reaction of readily available material, including various aromatic/aliphatic aldehydes and acetoacetanilide affording N , N ′‐diaryl‐2‐aryl‐6‐hydroxy‐6‐methyl‐4‐oxocyclohexane‐1,3‐dicarboxamides. The reaction proceeds at 50 °C under solvent‐free conditions via a one‐pot pseudo ‐three‐component reaction to yield functionalized cyclohexanones containing four quaternary stereogenic centers. Simple reaction conditions, moderate‐to‐high yields of product, no need of column chromatographic purification, eco‐friendliness, shorter reaction time, and simple work‐up has transformed this method an interesting route to the available procedures. The stereoselectivity of compounds was envisaged with crystallography and NMR spectroscopy.