Lithium binaphtholate-catalyzed michael reaction of malonates with maleates and its application to the enantioselective synthesis of tricarboxylic acid derivatives

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Abstract

The Michael reaction of malonates with maleates afforded the corresponding adducts in high yields with high enantioselectivities (up to 98% enantiomeric excess (ee)) by using dilithium 3,3′-dichlorobinaphtholate as a catalyst. The obtained Michael adducts could be converted to optically active tricarboxylic acid (TCA) derivatives via the Krapcho reaction.

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Sakamoto, M., Kaneko, T., Orito, Y., Shimoda, Y., & Nakajima, M. (2019). Lithium binaphtholate-catalyzed michael reaction of malonates with maleates and its application to the enantioselective synthesis of tricarboxylic acid derivatives. Chemical and Pharmaceutical Bulletin, 67(5), 452–460. https://doi.org/10.1248/cpb.c18-00993

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