期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 85, 期 2, 页码 985-993出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b02932
关键词
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资金
- Palackjr University [IGA_LF2019_019]
- Ministry of Health of the Czech Republic [17-31834A]
- European Regional Development Fund Project Centre for Experimental Plant Biology [CZ.02.1.01/0.0/0.0/16_019/0000738]
N-(3-Phenylprop-2-yn-1-yl)-sulfonamides derived from serine and threonine were synthesized using solid-phase synthesis and subjected to reaction with trimethylsilyl trifluoromethanesulfonate (TMSOTf). In contrast to the previously reported formation of 1,4-oxazepanes, this reaction afforded pyrrolidin-3-ones. A mechanistic explanation for this unexpected outcome is proposed, and the limitations and scope of the rearrangement are outlined.
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