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Control of Vicinal Stereocenters through Nickel‐Catalyzed Alkyl–Alkyl Cross‐Coupling
Author(s) -
Mu Xin,
Shibata Yu,
Makida Yusuke,
Fu Gregory C.
Publication year - 2017
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.201702402
Subject(s) - alkyl , vicinal , stereocenter , nickel , catalysis , coupling (piping) , chemistry , stereochemistry , organic chemistry , materials science , enantioselective synthesis , metallurgy
Vicinal stereocenters are found in many natural and unnatural compounds. Although metal‐catalyzed cross‐coupling reactions of unactivated alkyl electrophiles are emerging as a powerful tool in organic synthesis, there have been virtually no reports of processes that generate, much less control, vicinal stereocenters. In this investigation, we establish that a chiral nickel catalyst can mediate doubly stereoconvergent alkyl–alkyl cross‐coupling, specifically, reactions of a racemic pyrrolidine‐derived nucleophile with cyclic alkyl halides (as mixtures of stereoisomers) to produce vicinal stereocenters with very good stereoselectivity.