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Enantioselective synthesis of chiral α-thio-quaternary stereogenic centers via phase-transfer-catalyzed α-alkylation of α-acylthiomalonates : Enantioselective synthesis of chiral alpha-thio-quaternary stereogenic centers via phase-transfer-catalyzed alpha-alkylation of alpha-acylthiomalonates

Cited 4 time in Web of Science Cited 6 time in Scopus
Authors

Ha, Min Woo; Lee, Jun Young; Kim, Do Young; Lee, Geumwoo; Lee, Jae Kyun; Hong, Suckchang; Park, Hyeung-geun

Issue Date
2018-01
Publisher
American Chemical Society
Citation
Journal of Organic Chemistry, Vol.83 No.2, pp.1011-1018
Abstract
An efficient synthetic method for establishing chiral α-thio-α-quaternary stereogenic center was successfully developed. The enantioselective α-alkylation of α-acylthiomalonates under phase-transfer catalytic conditions [50% aq. KOH, toluene, −20 °C, and (S,S)-3,4,5-trifluorophenyl-NAS bromide] provided the corresponding α-acylthio-α-alkylmalonates in high chemical yields (up to 99%) and high optical yields (up to 98% ee).
ISSN
0022-3263
URI
https://hdl.handle.net/10371/202012
DOI
https://doi.org/10.1021/acs.joc.7b02605
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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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