Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 20, Pages 10016-10024Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01613
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Funding
- NSFC [21372002, 21232007]
- Open Foundation of Jiangsu Key Laboratory [K201314]
- JSNU
- PAPD of Jiangsu Province
- Qing Lan Project
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A catalytic chemo-, E/Z-, and enantioselective o-hydroxybenzyl alcohols with dimedone-derived enaminones has been established, which not only realized a chemoselective C1,2 cyclization of enaminones but also achieved the catalytic asymmetric construction of the biologically important tetrahydroxanthene framework with high E/Z- and enantioselectivities (all >95:5 E/Z, up to 98% yield, 97:3 er). This approach not only represents the first catalytic asymmetric C1,2 cyclization of enaminones with o-hydroxybenzyl alcohols but also provides an efficient strategy for constructing oxygenous heterocyclic frameworks with optical purity.
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