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Intramolecular Anodic Olefin Coupling Reactions: Use of the Reaction Rate To Control Substrate/Product Selectivity
Author(s) -
Xu HaiChao,
Moeller Kevin D.
Publication year - 2010
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.201003924
Subject(s) - chemistry , olefin fiber , substrate (aquarium) , pipecolic acid , selectivity , intramolecular force , amine gas treating , coupling reaction , photochemistry , catalysis , organic chemistry , amino acid , biochemistry , oceanography , geology
Look out—it's a trap! The anodic coupling of olefins with amine trapping groups to form proline and pipecolic acid derivatives with a quaternary α carbon atom (see scheme) was successful despite the significantly lower oxidation potential of the product relative to that of either functional group in the substrate: owing to the very fast cyclization, the oxidation potential of the substrate is lower than that of the product. Ts= p ‐toluenesulfonyl.
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