Enantioselective a-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis

Title
Enantioselective a-Alkylation of Benzylideneamino tert-Butyl Malonates by Phase-Transfer Catalysis
Authors
박정현하민우김병수홍석창김도영박요한김미현이재균이지연박형근
Keywords
asymmetric synthesis; enantioselectivity; phase-transfer catalysis; X-ray crystallographic structure
Issue Date
2015-09
Publisher
Advanced synthesis & catalysis
Citation
VOL 357, NO 13, 2841-2848
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/50606
ISSN
16154150
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KIST Publication > Article
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