Asymmetric Synthesis and Catalytic Activity of 3-Methyl-β-proline in Enantioselective anti-Mannich-type Reactions

K Nagata, Y Kuga, A Higashi, A Kinoshita…

Index: Nagata, Kazuhiro; Kuga, Yasushi; Higashi, Akinori; Kinoshita, Atsushi; Kanemitsu, Takuya; Miyazaki, Michiko; Itoh, Takashi Journal of Organic Chemistry, 2013 , vol. 78, # 14 p. 7131 - 7136

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Citation Number: 10

Abstract

Enantiomerically pure 3-methyl-β-proline was synthesized using an asymmetric phase- transfer-catalyzed alkylation of a cyanopropanoate to establish the all-carbon stereogenic center. The catalytic activity of 3-methyl-β-proline in the Mannich-type reaction between a glyoxylate imine and ketones/aldehydes was subsequently investigated. The catalyst was designed and found to be more soluble in nonpolar organic solvents relative to the ...