Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives

Midori Sakamoto; Tetsuya Kaneko; Yuya Orito; Yasushi Shimoda; Makoto Nakajima

doi:10.1248/cpb.c18-00993

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Lithium Binaphtholate-Catalyzed Michael Reaction of Malonates with Maleates and Its Application to the Enantioselective Synthesis of Tricarboxylic Acid Derivatives

Midori Sakamoto, Tetsuya Kaneko, Yuya Orito, Yasushi Shimoda , Makoto Nakajima

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Keywords: Michael reaction, lithium binaphtholate, tricarboxylic acid ester, Krapcho reaction, stereoselectivity

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2019 Volume 67 Issue 5 Pages 452-460

DOI https://doi.org/10.1248/cpb.c18-00993

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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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