Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates

Title
Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates
Authors
하민우이명모최수지김식홍석창박요한김미현김택수이지훈이재균박형근
Keywords
α-amido-α-alkylmalonates; phase-transfer catalytic α- alkylation; X-ray crystallographic structure; alkylating agents
Issue Date
2015-03
Publisher
Journal of organic chemistry
Citation
VOL 80, NO 6, 3270-3279
Abstract
An efficient enantioselective synthetic method for alpha-amido-alpha-alkylmalonates via phase-transfer catalytic alpha-alkylation was successfully developed. The alpha-alkylation of alpha-amidomalonates under phase-transfer catalytic conditions (50% KOH, toluene, -40 degrees C) in the presence of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded the corresponding alpha-amido-alpha-alkylmalonates in high chemical yields (up to 99%) and optical yields (up to 97% ee), which could be readily converted to versatile chiral intermediates bearing alpha-amino quaternary stereogenic centers. The synthetic potential of this methodology was demonstrated via the synthesis of chiral azlactone, oxazoline, and unnatural alpha-amino acid.
URI
http://pubs.kist.re.kr/handle/201004/50603
ISSN
00223263
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KIST Publication > Article
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