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Oxidative Nucleophilic Substitution of Hydrogen in Nitroarenes with Carbanions of Protected Serine and Threonine Esters
Author(s) -
Sulikowski Daniel,
Mąkosza Mieczysław
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000498
Subject(s) - chemistry , carbanion , threonine , serine , adduct , medicinal chemistry , stereochemistry , organic chemistry , enzyme
The reactions of carbanions of protected serine and threonine esters with nitroarenes were studied. The main process involves the addition of the carbanions to the para position of the nitroarenes, which is occupied by a hydrogen atom, to form σ H adducts that are subsequently oxidized by 2,3‐dichloro‐5,6‐dicyanobenzoquinone to give p ‐nitroaryl derivatives of the protected serine and threonine. Oxidation of the σ H adducts with dimethyldioxirane resulted in the formation of the corresponding p ‐hydroxyaryl derivatives of these amino acids. Addition of the carbanions of the protected threonine ester is a highly stereoselective process controlled by the second chiral center of threonine.