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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
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Cited 18 time in Scopus
- Authors
- 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
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