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Quinine‐Catalysed Double Michael Addition of Malononitrile to 1,5‐Disubstituted Pentadien‐3‐ones: A Stereoselective Route to Cyclohexanones
Author(s) -
De Fusco Claudia,
Lattanzi Alessandra
Publication year - 2011
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.201100282
Subject(s) - malononitrile , chemistry , stereoselectivity , cyclohexane , michael reaction , pyran , quinine , cascade , organic chemistry , stereochemistry , medicinal chemistry , catalysis , chromatography , malaria , immunology , biology
The stereoselective synthesis of 4‐oxo‐2,6‐diaryl‐cyclohexane‐1,1‐dicarbonitriles has been developed through double Michael addition of malononitrile to 1,5‐disubstituted pentadien‐3‐ones catalysed by quinine. This simple cascade process affords cyclohexanones in moderate‐to‐good yields, excellent diastereoselectivity and up to 86 % ee . The isolation of the monoaddition product helps to shed light on thestereochemical outcome of the two‐step process.