1427203-57-3Relevant 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 (2013/08/23)
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.
A stereoselective cyclization strategy for the preparation of γ-lactams and their use in the synthesis of α-Methyl-β-proline
Banerjee, Souvik,Smith, Justin,Smith, Jillian,Faulkner, Caleb,Masterson, Douglas S.
, p. 10925 - 10930 (2013/02/22)
A straightforward stereoselective and enantiodivergent cyclization strategy for the construction of γ-lactams is described. The cyclization strategy makes use of chiral malonic esters prepared from enantiomerically enriched monoesters of disubstituted malonic acid. The cyclization occurs with the selective displacement of a substituted benzyl alcohol as the leaving group. A Hammett study illustrates that the cyclization is under electronic control. The resulting γ-lactam can be readily converted into a novel proline analogue.
