Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates
- Construction of Chiral alpha-Amino Quaternary Stereogenic Centers via Phase-Transfer Catalyzed Enantioselective alpha-Alkylation of alpha-Amidomalonates
- 하민우; 이명모; 최수지; 김식; 홍석창; 박요한; 김미현; 김택수; 이지훈; 이재균; 박형근
- α-amido-α-alkylmalonates; phase-transfer catalytic α-
alkylation; X-ray crystallographic structure; alkylating agents
- Issue Date
- Journal of organic chemistry
- VOL 80, NO 6, 3270-3279
- 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.
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