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Gold-catalyzed transannular [4+3] cycloaddition reactions.

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.

SUBMITTER: Gung BW

PROVIDER: S-EPMC3539418 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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Gold-catalyzed transannular [4+3] cycloaddition reactions.

Gung Benjamin W BW Craft Derek T DT Bailey Lauren N LN Kirschbaum Kristin K

Chemistry (Weinheim an der Bergstrasse, Germany) 20100101 2

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. ...[more]

PMID: 19937623

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