A Practical Strategy for the Structural Diversification of Aliphatic Scaffolds through the Palladium-Catalyzed Picolinamide-Directed Remote Functionalization of Unactivated C(sp3)H Bonds

Hats off to the director: High levels of regio‐ and stereoselectivity were observed for a broad range of amine substrates with aryl and vinyl iodide coupling partners in the title reaction. The synthetic utility of this strategy was highlighted by the ready preparation from threonine of 1, with a re...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2011-05, Vol.50 (22), p.5192-5196
Main Authors: He, Gang, Chen, Gong
Format: Article
Language:English
Subjects:
alkenylation
arylation
CH activation
directing groups
Palladium
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Summary:Hats off to the director: High levels of regio‐ and stereoselectivity were observed for a broad range of amine substrates with aryl and vinyl iodide coupling partners in the title reaction. The synthetic utility of this strategy was highlighted by the ready preparation from threonine of 1, with a removable picolinamide auxiliary PAr, and its coupling with 2 in a concise formal synthesis of (+)‐obafluorin. TBS=tert‐butyldimethylsilyl.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201100984