Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 6, Pages 2598-2606Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02725
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Funding
- National Natural Science Foundation of China [21572083, 21322201, 21290180]
- Fundamental Research Funds for the Central Universities [lzujbky-2015-48, lzujbky-2013-ct02]
- State Key Laboratory of Natural and Biomimetic Drugs [K20150213]
- PCSIRT [IRT_15R28]
- 111 Project of Ministry of Education of China [111-2-17]
- Chang Jiang Scholars Program
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A novel DBU-mediated stereoselective spirocyclopropanation of para-quinone methides with sulfonium salts has been developed on the basis of the mode involving a 1,6-conjugate addition/intramolecular dearomatizing cyclization cascade. This reaction provides a mild and effective method for the assembly of synthetically and structurally interesting spirocyclopropanyl para-dienones. The feasibility for the enantioselective access to such functionalized para-dienones has also been explored by using the axially chiral sulfonium salt. Importantly, the regioselective ring openings of the related spirocyclopropanyl para-dienones have been achieved divergently.
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