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Enantioselective Alkylation of Acyclic α,α‐Disubstituted Tributyltin Enolates Catalyzed by a {Cr(salen)} Complex
Author(s) -
Doyle Abigail G.,
Jacobsen Eric N.
Publication year - 2007
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.200604901
Subject(s) - enantioselective synthesis , stereocenter , chemistry , alkylation , ethylenediamine , cationic polymerization , tributyltin , catalysis , halide , yield (engineering) , medicinal chemistry , organic chemistry , stereochemistry , materials science , metallurgy
Straighten out the mixture : A dynamic mixture of acyclic isomers of tributyltin enolates undergoes a {Cr(salen)}‐catalyzed alkylation reaction to generate methyl ketones that contain α‐carbonyl quaternary stereocenters in high yield and enantioselectivity (salen= N , N ′‐bis(salicylidene)ethylenediamine dianion). A mechanism is proposed which involves halide activation by a cationic metal complex.