Zinc‐Catalyzed Tandem Diels–Alder Reactions of Enynals with Alkenes: Generation and Trapping of Cyclic  o ‐Quinodimethanes ( o ‐QDMs) | Zendy

Zhang Jiantao | Zendy; Xiao Yelin | Zendy; Chen Kai | Zendy; Wu Wanqing | Zendy; Jiang Huanfeng | Zendy; Zhu Shifa | Zendy

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Zinc‐Catalyzed Tandem Diels–Alder Reactions of Enynals with Alkenes: Generation and Trapping of Cyclic o ‐Quinodimethanes ( o ‐QDMs)

Author(s) -

Zhang Jiantao,

Xiao Yelin,

Chen Kai,

Wu Wanqing,

Jiang Huanfeng,

Zhu Shifa

Publication year - 2016

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.201600266

Subject(s) - cycloaddition , chemistry , catalysis , zinc , tandem , trapping , selectivity , diels–alder reaction , photochemistry , medicinal chemistry , organic chemistry , materials science , ecology , composite material , biology

A systematic investigation of ZnCl 2 ‐catalyzed reactions of enynals with alkenes has been undertaken. Structurally unique propeller‐like products could be obtained under mild conditions. Cyclic o ‐quinodimethanes ( o ‐QDMs) are generated through [4+2] cycloaddition between enynals and alkenes. Both electron‐poor and electron‐rich dienophiles could be used to trap the active intermediate through [4+2] cycloaddition. But [1,5]‐H shift products could also be observed when electron‐rich alkenes were used as dienophile. DFT calculations were performed to understand the reaction mechanism. A competition between the [4+2] cycloaddition and [1,5]‐H shift was proposed for the transformation of cyclic o ‐QDMs. The selectivity could be affected by the properties of the substrates.

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