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†,10.1039/C3RA40965A

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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†

B. V. Subba Reddy,Manisha Swain,S. Madhusudana Reddy,J. S. Yadav

RSC Advances Pub Date : 03/27/2013 00:00:00 , DOI:10.1039/C3RA40965A

Abstract

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.