Metathesis Reaction of Diazo Compounds and para-Quinone Methides for C–C Double Bond Formation: Synthesis of Tetrasubstituted Alkenes and Quinolinones

The para-quinone methides (p-QMs) are activated by Lewis acid and then attacked by diazo compounds. The following rearrangement leads to nitrogen gas extrusion and C–C double bond formation to constitute a metathesis reaction process. Therefore, the diazoester is transformed into tetrasubstituted al...

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Bibliographic Details
Published in:Organic letters 2016-10, Vol.18 (19), p.4888-4891
Main Authors: Huang, Bo, Shen, Yangyong, Mao, Zhenjun, Liu, Yu, Cui, Sunliang
Format: Article
Language:English
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Summary:The para-quinone methides (p-QMs) are activated by Lewis acid and then attacked by diazo compounds. The following rearrangement leads to nitrogen gas extrusion and C–C double bond formation to constitute a metathesis reaction process. Therefore, the diazoester is transformed into tetrasubstituted alkenes, whereas the diazo-oxindole delivers the quinolinone products. Furthermore, the 13C-labeling experiments were also conducted to elucidate a possible mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b02365