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Abstract

SELECTIVE FORMATION OF DIELS-ALDER ADDUCTS IN AQUEOUS MEDIA USING CHIRAL BENZIMIDAZOLES: INVESTIGATION THROUGH CHIRAL HPLC

Pallavi Tiwari Roy, Trupti Tawde, Vaibhav P. Landage and Nitin A. Mirgane*

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Abstract

Reactions between anthrone and alkyl/aryl maleimide catalyzed by benzimidazole derived chiral Bronsted bases led to the formation of an unexpected Diels-Alder (D-A) adduct instead of Michael adduct in aqueous ethanol. An excellent yield was observed within a short period of time. Chiral HPLC analysis at different reaction times was used to confirm the formation of the unexpected Diels-Alder (D-A) adduct.

Keywords: Diels-Alder, Bronsted base, Michael adduct, chiral HPLC.


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