Organic Letters
Organic Letters
4 years ago

Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group

Catalytic Asymmetric Cycloadditions of Silyl Nitronates Bearing α-Aryl Group
Juanjuan Feng, Minghui Jiang, Lifei Feng, Peng Jiao
1,3-Dipolar cycloadditions of 2-alkylacroleins or atropaldehyde with triisopropylsilyl nitronates bearing an α-aryl group produced 3-aryl-2-isoxazolines having a chiral quaternary center in up to 94% ee and up to 88% yield with the aid of Corey’s oxazaborolidine catalyst. Specifically, the TIPS nitronate with an α-(p-methoxyphenyl) group gave mainly the 2-isoxazolines having an all-carbon quaternary center.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00558

DOI: 10.1021/acs.orglett.7b00558

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