Cu(ii)-Catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) and electron-poor 3-vinylindoles

A new Cu(ii)-catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) including para-quinone methides (p-QMs) and ortho-quinone methides (o-QMs) and electron-poor 3-vinylindoles was established. A wide range of richly decorated indole-containing chromane derivatives were synthesized in...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2020-01, Vol.7 (2), p.414-419
Main Authors: Hong-Ming, Huang, Xu-Yan, Wu, Bo-Rong Leng, Yi-Long, Zhu, Xin-Chao, Meng, Yu, Hong, Jiang, Bo, De-Cai, Wang
Format: Article
Language:English
Subjects:
Copper
Crystallography
Cycloaddition
Indoles
Organic chemistry
Quinones
Stereoselectivity
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Summary:A new Cu(ii)-catalyzed formal [4 + 2] cycloaddition between quinone methides (QMs) including para-quinone methides (p-QMs) and ortho-quinone methides (o-QMs) and electron-poor 3-vinylindoles was established. A wide range of richly decorated indole-containing chromane derivatives were synthesized in acceptable yields and diastereoselectivity. Based on several control experiments, a possible mechanism was also proposed to elucidate the catalytic cycle pathway.
ISSN:2052-4110
2052-4110
DOI:10.1039/c9qo01343a