(3S,4R)-3,4-Dihydroxy-N-alkyl-L-homoprolines: Synthesis and Computational Mechanistic Studies
This is the first synthetic report of (3S,4R)-dihydroxy-N-alkyl-L-homoprolines described so far. 2,4-O-Benzylidene-D-erythrose was obtained from D-glucose with an improved yield, and then transformed into the title (3S,4R)-dihydroxy-N-alkyl-L-homoprolines, in a two-step strategy, with excellent overall yields. Hydrogenolysis of the benzyl group led to the NH congener. The synthesis of final products from 1,4-lactone intermediates was studied by computational means either in acidic and basic conditions. The theoretical mechanism’s studies full explain the experimental results: a) an equilibrium between L-homoprolines and its bicyclic counterpart is established in acid; b) the equilibrium suffers a complete displacement towards the L-homoprolines side in basic medium.
- This article is part of the themed collection: Mechanistic, computational & physical organic chemistry in OBC