Title: Rational design of highly diastereoselective, organic base-catalyzed, room-temperature Michael addition reactions
Authors: Soloshonok, VA ×
Cai, CZ
Hruby, VJ
Van Meervelt, Luc
Yamazaki, T #
Issue Date: Jan-2000
Publisher: Amer chemical soc
Series Title: Journal of Organic Chemistry vol:65 issue:20 pages:6688-6696
Abstract: Via the rational design of a single-preferred transition state, stabilized by electron donor-acceptor-type attractive interactions, structural and geometric requirements for the Corresponding starting compounds have been determined. The Ni(II) complex of the Schiff base of glycine with o-[N-alpha-picolylamino]acetophenone, as a nucleophilic glycine equivalent, and N-(trans-enoyl)oxazolidin-2-ones, as derivatives of an alpha,beta-unsaturated carboxylic acid, were found to be the substrates of choice featuring geometric/conformational homogeneity and high reactivity. The corresponding Michael addition reactions were found to proceed at room temperature in the presence of catalytic amounts of DBU to afford quantitatively the addition pro ducts with virtually complete diastereoselectivity. Acidic decomposition of the products followed by treatment of the reaction mixture with NH4OH gave rise to the diastereomerically pure 3-substituted pyroglutamic acids.
ISSN: 0022-3263
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Biochemistry, Molecular and Structural Biology Section
× corresponding author
# (joint) last author

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