Enantioselective Alkylation of Acyclic α,α‐Disubstituted Tributyltin Enolates Catalyzed by a {Cr(salen)} Complex | Zendy

Doyle Abigail G. | Zendy; Jacobsen Eric N. | Zendy

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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.

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