期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 25, 页码 8661-8666出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b03782
关键词
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资金
- RIKEN
- National Institutes of General Medical Sciences [17H02213, R35 GM118055]
- NSF EAPSI/JSPS
- Grants-in-Aid for Scientific Research [17H02213] Funding Source: KAKEN
An enantioselective [3 + 2] cycloaddition reaction between nitrile oxides and transiently generated enolates of a-keto esters has been developed. The catalyst system was found to be compatible with in situ nitrile oxide generation conditions. A versatile array of nitrile oxides and alpha-keto esters could participate in the cycloaddition, providing novel S-hydroxy-2-isoxazolines in high chemical yield with high levels of diastereo- and enantioselectivity. Notably, the optimal reaction conditions circumvented concurrent reactions via O-imidoylation and hetero-[3 + 2] pathways.
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