1446482-09-2Relevant articles and documents
Asymmetric synthesis and catalytic activity of 3-methyl-β-proline in enantioselective anti -mannich-type reactions
Nagata, Kazuhiro,Kuga, Yasushi,Higashi, Akinori,Kinoshita, Atsushi,Kanemitsu, Takuya,Miyazaki, Michiko,Itoh, Takashi
, p. 7131 - 7136 (2013)
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 unsubstituted β-proline catalyst, and as a result allowed for added flexibility during optimization efforts. This work culminated in the development of a highly anti-diastereo- and enantioselective process employing low catalyst loading.