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A Practical Strategy for the Structural Diversification of Aliphatic Scaffolds through the Palladium‐Catalyzed Picolinamide‐Directed Remote Functionalization of Unactivated C(sp 3 )H Bonds
Author(s) -
He Gang,
Chen Gong
Publication year - 2011
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.201100984
Subject(s) - palladium , surface modification , stereoselectivity , aryl , amine gas treating , catalysis , chemistry , iodide , combinatorial chemistry , organic chemistry , alkyl
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.