Diastereoselective beta-hydroxyalkylation and beta-hydroxycarboxylation of amides by a Diels-Alder strategy
(2002) Synthesis : journal of synthetic organic chemistry — n° 14, p. 2043-2052 (2002)
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- Acid chlorides readily condensed with N-silylated imines in the presence of a base to generate 2-azadienes. These underwent Diels-Alder cycloadditions with a wide variety of aldehydes.. In most cases the cycloadditions were diastereoselective in favor of the 3,4-cis-oxazinone adducts. Ethanolysis stereoselectively yielded products of hydroxyalkylation or hydroxycarboxylation of the primary amides derived from the initial acid chlorides.
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Ntirampebura, D., & Ghosez, L. (2002). Diastereoselective beta-hydroxyalkylation and beta-hydroxycarboxylation of amides by a Diels-Alder strategy. Synthesis : journal of synthetic organic chemistry, 14, 2043-2052. https://hdl.handle.net/2078.5/45528 (Original work published 2002)