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Regioselective Cyclizations Utilizing a Gold‐Catalyzed [3,3] Propargyl Ester Rearrangement
Author(s) -
Cran John W.,
Krafft Marie E.
Publication year - 2012
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.201203923
Subject(s) - regioselectivity , propargyl , sigmatropic reaction , zwitterion , chemistry , catalysis , stereochemistry , organic chemistry , molecule
Switch‐Au‐roo : A new strategy for the regioselective synthesis of unsaturated carbocycles by chemoselective activation of a Rauhut–Currier zwitterion surrogate, formed from the Au‐catalyzed [3,3] sigmatropic rearrangement of propargylic esters, has been achieved. By reversing the regiochemistry of the propargyl ester the synthesis of either the endo‐ or exocyclic enones is feasible.