Premium
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.