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Enantioselective synthesis of chiral α-azido and α-aryloxy quaternary stereogenic centers via the phase-transfer-catalyzed α-alkylation of α-bromomalonates, followed by SN2 substitution : Enantioselective synthesis of chiral alpha-azido and alpha-aryloxy quaternary stereogenic centers via the phase-transfer-catalyzed alpha-alkylation of alpha-bromomalonates, followed by SN2 substitution

Cited 17 time in Web of Science Cited 18 time in Scopus
Authors

Kim, Doyoung; Ha, Min Woo; Hong, Suck Chang; Park, Cheonhyoung; Kim, Byungsoo; Yang, Jewon; Park, Hyeung-Geun

Issue Date
2017-05
Publisher
American Chemical Society
Citation
Journal of Organic Chemistry, Vol.82 No.9, pp.4936-4943
Abstract
A new efficient synthetic method for chiral alpha-azido-alpha-alkylmalonates and alpha-aryloxy-alpha-alkylmalonates was developed. The enantioselective alpha-alkylation of diphenylmethyl tert-butyl alpha-bromomalonate under phase-transfer catalytic conditions [(S,S)-3,4,5-trifluorophenyl-NAS bromide, 50% KOH, toluene, and -40 degrees C) provided the corresponding alpha-bromo-alpha-alkylmalonates in high chemical yields (<= 98%) and high optical yields (<= 99% ee). The resulting alpha-alkylated products were converted to alpha-azido-alpha-alkylmalonates <= 97% ee) and alpha-aryloxy-alpha-alkylmalonates (<= 79%, <= 93%, ee) by S(N)2 substitution with sodium azide and aryloxides, respectively.
ISSN
0022-3263
URI
https://hdl.handle.net/10371/202013
DOI
https://doi.org/10.1021/acs.joc.7b00324
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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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