期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 9, 页码 4936-4943出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00324
关键词
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资金
- National Research Foundation of Korea [2016R1A2B2008109]
- BK21 Plus Program
- National Research Foundation of Korea [2016R1A2B2008109] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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.
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