Enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone and 1,3-dicarbonyls to β-nitroalkenes catalyzed by a novel bifunctional rosin-indane amine thiourea catalyst
2013
Reddy, B. V Subba | Swain, Manisha | Reddy, S Madhusudana | Yadav, J. S.
A novel bifunctional rosin-derived indane amine thiourea organocatalyst has been prepared and evaluated its catalytic efficiency in enantioselective Michael addition of 2-hydroxy-1,4-naphthoquinone to β-nitrostyrenes. 3-Alkylnitro-2-hydroxy-1,4-naphthoquinones are obtained remarkably with high enantioselectivities (87–99% ee) and in good yields using low catalyst loading (1 mol%). The catalyst was also found to be effective in catalyzing asymmetric Michael addition of pentane-1,3-dione to trans-β-nitroalkenes.
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