Premium
Gold‐Catalyzed Oxidative Cyclizations on 1,4‐Enynes: Evidence for a γ‐Substituent Effect on Wagner–Meerwein Rearrangements
Author(s) -
Ghorpade Satish,
Su MingDer,
Liu RaiShung
Publication year - 2013
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.201210313
Subject(s) - substituent , chemistry , stereospecificity , oxidative phosphorylation , context (archaeology) , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , paleontology , biology
Gold ‐catalyzed oxidative cyclizations of 1,4‐enynes were used to study the γ‐effect on the Wagner–Meerwein rearrangement. Both experimental and theoretical work disclose that a gold substituent in the γ‐position can direct a stereospecific 1,2‐shift of the anti ‐β‐substituent regardless of its intrinsic properties.