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Gold‐Catalyzed Cycloisomerization of Cyclopropyl Alkynyl Acetates: A Versatile Approach to 5‐, 6‐, and 7‐Membered Carbocycles
Author(s) -
Zou Yue,
Garayalde David,
Wang Quanrui,
Nevado Cristina,
Goeke Andreas
Publication year - 2008
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.200804202
Subject(s) - cycloisomerization , carbocation , chirality (physics) , propargyl , chemistry , cationic polymerization , catalysis , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Nonclassical chirality transfer? Depending on the substitution pattern of propargyl acetates, a gold‐catalyzed homologous Rautenstrauch reaction generates either 5‐ or 6‐membered ring systems (see scheme). The stabilization of cationic intermediates is crucial for this reaction to succeed. The underlying principle for the good chirality transfer observed could be gold‐stabilized nonclassical carbocations having configurational stability.