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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

Cited 14 time in Web of Science Cited 16 time in Scopus
Authors

Ha, Min Woo; Lee, Myungmo; Choi, Sujee; Kim, Seek; Hong, Suckchang; Park, Yohan; Kim, Mi-hyun; Kim, Taek-Soo; Lee, Jihoon; Lee, Jae Kyun; Park, Hyeung-geun

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
URI
https://hdl.handle.net/10371/202020
DOI
https://doi.org/10.1021/jo502791d
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  • College of Pharmacy
  • Department of Manufacturing Pharmacy
Research Area Development of methodologies using metal catalyst, Total synthesis of natural products

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