Park, Cheonhyoung Ha, Min Woo Kim, Byungsoo Hong, Suckchang Kim, Doyoung Park, Yohan Kim, Mi-hyun Lee, Jae Kyun Lee, Jeeyeon Park, Hyeung-geun 2024-01-20T06:03:57Z 2024-01-20T06:03:57Z 2021-09-05 2015-09-14 1615-4150 https://pubs.kist.re.kr/handle/201004/125023 A new enantioselective synthetic method for the synthesis of alpha,alpha-dialkylmalonates with a quaternary carbon center was developed via alpha-alkylation of prochiral malonates by phase-transfer catalysis (PTC). Asymmetric alpha-alkylation of benzylideneamino tert-butyl alpha-methylmalonates under phase-transfer catalytic conditions in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding alpha,alpha-dialkylmalonates in high yields (up to 97%) with excellent enantioselectivities (up to 98% ee). The products were then selectively hydrolyzed to chiral malonic monoacids under basic, acidic, or catalytic hydrogenation conditions. English WILEY-V C H VERLAG GMBH ASYMMETRIC ALKYLATION STEREOSELECTIVE-SYNTHESIS 1,3-DICARBONYL COMPOUNDS CONJUGATE ADDITION MICHAEL ADDITIONS CARBON CENTER AMINO-ACIDS CONSTRUCTION DESYMMETRIZATION FLUORINATION Enantioselective alpha-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis Article 10.1002/adsc.201500560 1 ADVANCED SYNTHESIS & CATALYSIS, v.357, no.13, pp.2841 - 2848 ADVANCED SYNTHESIS & CATALYSIS 357 13 2841 2848 scie scopus 000362527100011 2-s2.0-84941804379 Chemistry, Applied Chemistry, Organic Chemistry Article ASYMMETRIC ALKYLATION STEREOSELECTIVE-SYNTHESIS 1,3-DICARBONYL COMPOUNDS CONJUGATE ADDITION MICHAEL ADDITIONS CARBON CENTER AMINO-ACIDS CONSTRUCTION DESYMMETRIZATION FLUORINATION asymmetric synthesis alpha,alpha-dialkylmalonates enantioselectivity phase-transfer catalysis PTC