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Interception of a Rautenstrauch Intermediate by Alkynes for [5+2] Cycloaddition: Rhodium‐Catalyzed Cycloisomerization of 3‐Acyloxy‐4‐ene‐1,9‐diynes to Bicyclo[5.3.0]decatrienes
Author(s) -
Shu Xingzhong,
Huang Suyu,
Shu Dongxu,
Guzei Ilia A.,
Tang Weiping
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201103136
Subject(s) - cycloisomerization , bicyclic molecule , rhodium , cycloaddition , intramolecular force , chemistry , ene reaction , ring (chemistry) , catalysis , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry
Rholling in the bicycles : A rhodium(I)‐catalyzed cycloisomerization for the synthesis of bicyclic compounds containing a cycloheptatriene ring from linear alkenynes (see scheme; cod=1,5‐cyclooctadiene) is proposed to proceed through 1,2‐acyloxy migration, 6 π electrocyclization, migratory insertion, and reductive elimination. The overall process can be viewed as a novel intramolecular [5+2] cycloaddition with concomitant 1,2‐acyloxy migration.