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Construction of chiral α-amino quaternary stereogenic centers via phase-transfer catalyzed enantioselective α-alkylation of α-amidomalonates : Construction of chiral alpha-amino quaternary stereogenic centers via phase-transfer catalyzed enantioselective alpha-alkylation of alpha-amidomalonates
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Cited 16 time in Scopus
- Authors
- Issue Date
- 2015-03
- Publisher
- American Chemical Society
- Citation
- Journal of Organic Chemistry, Vol.80 No.6, pp.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.
- ISSN
- 0022-3263
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