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Unexpected Diastereoselective Acetylation of 1,8‐Dimethoxyanthracene Adducts with Maleic Anhydride and Dimethyl Maleate
Author(s) -
Sereda Grigoriy A.,
Moorthy Ramkumar,
Basa Prem N.,
Sykes Andrew G.,
Purohit Kaushalkumar,
Rajpara Vikul B.,
Becht Dustin C.
Publication year - 2012
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.201101399
Subject(s) - chemistry , maleic anhydride , adduct , steric effects , stereoselectivity , diastereomer , acetylation , benzene , medicinal chemistry , stereochemistry , organic chemistry , polymer chemistry , polymer , catalysis , biochemistry , copolymer , gene
Friedel–Crafts acetylation of adducts between 1,8‐dimethoxyanthracene and maleic anhydride or dimethyl maleate proceeds with a strong preference toward the syn diastereomer. This stereoselectivity is especially prominent for the anhydride counterpart. Dependence of the observed selectivity on the adduct structure is rationalized by the analysis of computed HOMO energies of the reactants and relative energies of the intermediate σ‐complexes. The possible undesired intermolecular condensation of the anhydride did not take place because of steric hindrance. Structures of the reaction products were unambiguously confirmed by single‐crystal X‐ray diffraction (XRD). The reported stereoselectivity of acetylation provides facile access to compounds with the functionalized benzene ring in a syn arrangement with respect to the pendant carboxyl substituents.