Chiral Ionic Liquid Mediated Diels-Alder Reaction Between Anthrone Enolate and Maleimides

Author(s): Nitin A. Mirgane, Mohammed Hasan H. Akhtar, Anil V. Karnik.

Journal Name: Letters in Organic Chemistry

Volume 7 , Issue 4 , 2010

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A chiral ionic liquid, 1-butyl-3-methylimidazolium (T-4)-bis[(2S)-2-(hydroxy-κO) propanoato-κO]borate (BMIm+BLLB-), has been used as organocatalyst and asymmetric inducer in Diels-Alder reactions between anthrone and various maleimides. This greener solvent makes the reaction faster, proceeds with quantitative yields and exhibits moderate enantioselectivity. Stereochemical outcome suggests a more organized transition state in ionic liquid involving hydrogen bonding and polar interactions.

Keywords: Chiral ionic liquid, diels-alder reaction, bronsted base, green solvents, enantioselective, HPLC

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Article Details

Year: 2010
Page: [343 - 347]
Pages: 5
DOI: 10.2174/157017810791130559
Price: $65

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