Enantioselective alpha-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis
- Authors
- Park, Cheonhyoung; Ha, Min Woo; Kim, Byungsoo; Hong, Suckchang; Kim, Doyoung; Park, Yohan; Kim, Mi-hyun; Lee, Jae Kyun; Lee, Jeeyeon; Park, Hyeung-geun
- Issue Date
- 14-Sep-2015
- Publisher
- WILEY-V C H VERLAG GMBH
- Keywords
- asymmetric synthesis; alpha,alpha-dialkylmalonates; enantioselectivity; phase-transfer catalysis; PTC
- Citation
- ADVANCED SYNTHESIS & CATALYSIS, v.357, no.13, pp.2841 - 2848
- Journal Title
- ADVANCED SYNTHESIS & CATALYSIS
- Volume
- 357
- Number
- 13
- Start Page
- 2841
- End Page
- 2848
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/10152
- DOI
- 10.1002/adsc.201500560
- ISSN
- 1615-4150
- Abstract
- 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.
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