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Gold‐Catalyzed Transannular [4+3] Cycloaddition Reactions
Author(s) -
Gung Benjamin W.,
Craft Derek T.,
Bailey Lauren N.,
Kirschbaum Kristin
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200902185
Subject(s) - cycloaddition , propargyl , regioselectivity , chemistry , furan , ring (chemistry) , catalysis , tandem , medicinal chemistry , stereochemistry , organic chemistry , materials science , composite material
Abstract Macrocyclic propargyl acetates containing a furan ring were prepared by using a CrCl 2 ‐promoted reaction. In the presence of either a Au I or Au III catalyst, a tandem 3,3‐rearrangement/transannular [4+3] cycloaddition reaction occurred to give propargyl acetates that are regio‐ and diastereospecific. The regiochemistry of the product is controlled by the position of the acetoxy group in the starting material and the stereochemistry of the reaction depends on the ring size.