Enantioselective a-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis
- Enantioselective a-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis
- 박정현; 하민우; 김병수; 홍석창; 김도영; 박요한; 김미현; 이재균; 이지연; 박형근
- asymmetric synthesis; enantioselectivity; phase-transfer catalysis; X-ray crystallographic structure
- Issue Date
- Advanced synthesis & catalysis
- VOL 357, NO 13, 2841-2848
- A new enantioselective synthetic method for the synthesis of α,α-dialkylmalonates with a quaternary carbon center was developed via α-alkylation of prochiral malonates by phase-transfer catalysis (PTC). Asymmetric α-alkylation of benzylideneamino tert-butyl α-methylmalonates under phase-transfer catalytic conditions in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding α,α-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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