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Regio‐ and Stereoselective [4+3] Cycloaddition Towards Fused 5,7,6‐Tricyclic Skeletons
Author(s) -
Gong Wanchun,
Liu Yun,
Zhang Jie,
Jiao Yingdong,
Xue Jijun,
Li Ying
Publication year - 2013
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201201066
Subject(s) - cycloaddition , furan , pyrrole , thiophene , chemistry , ring (chemistry) , tricyclic , stereoselectivity , allylic rearrangement , stereochemistry , combinatorial chemistry , computational chemistry , organic chemistry , catalysis
Ringer! Multi‐ring‐fused structures with 7‐membered carbocycles are often elusive because of 7‐membered ring strain and entropy. The [4+3] cycloaddition reaction between the allylic cation of a heterocyclic alcohol and a conjugated diene yields the 7‐membered ring of 5,7,6‐tricyclic structures. Skeletons with furan were constructed in the presence of Tf 2 O/2,6‐lutidine, while reactions with thiophene and pyrrole proceeded in the presence of Tf 2 O/2,6‐lutidine or ZnCl 2 .