Concise Construction of Bicyclo[6.4.0] and ‐[7.4.0] Frameworks by [4+2] Cycloaddition of 3,4‐Dimethylene‐2,5‐bis(phenylsulfonyl)cycloalk‐1‐enes | Zendy

Mukai Chisato | Zendy; Ueda Masanobu | Zendy; Takahashi Yasuhito | Zendy; Inagaki Fuyuhiko | Zendy

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Concise Construction of Bicyclo[6.4.0] and ‐[7.4.0] Frameworks by [4+2] Cycloaddition of 3,4‐Dimethylene‐2,5‐bis(phenylsulfonyl)cycloalk‐1‐enes

Author(s) -

Mukai Chisato,

Ueda Masanobu,

Takahashi Yasuhito,

Inagaki Fuyuhiko

Publication year - 2015

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201500598

Subject(s) - bicyclic molecule , chemistry , cycloaddition , vicinal , carbon skeleton , methylene , cyclobutene , medicinal chemistry , intermolecular force , stereochemistry , organic chemistry , molecule , ring (chemistry) , catalysis

The thermal intermolecular [4+2] cycloadditions of vicinal bis( exo ‐methylene)cyclooctene with carbon dienophiles efficiently produce the bicyclo[6.4.0] framework. Similar cycloadditions with the one‐carbon‐homologated cyclononene derivatives result in the formation of the bicyclo[7.4.0] skeleton. Both aza‐ and oxadieonphiles are suitable for this [4+2] reaction and provide the corresponding hetero‐Diels–Alder‐type products.

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