Diastereodivergent synthesis of chiral tetrahydropyrrolodiazepinediones via a one-pot intramolecular aza-Michael/lactamization sequence
Panek, James S.
Porco, John A.
Brown, Lauren E.
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Citation (published version)Spandan Chennamadhavuni, James S Panek, John A Porco, Lauren E Brown. 2018. "Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones via a One-Pot Intramolecular aza-Michael/Lactamization Sequence." JOURNAL OF ORGANIC CHEMISTRY, Volume 83, Issue 24, pp. 15449 - 15462 (14). https://doi.org/10.1021/acs.joc.8b02724
A modular and diastereodivergent synthesis of tetrahydro-1H-pyrrolo[1,2d]diazepine-(2,5)-diones is presented. The tetrahydropyrrolodiazepinedione scaffold is obtained via a base-mediated three-step isomerization/tandem cyclization of amino acid-coupled homoallylic amino esters. Diastereoselectivity of the process is mediated by the interplay of a kinetic cyclization event and a propensity for thermodynamic epimerization at two labile chiral centers, giving rise to two distinct major diastereomers dependent on starting material stereochemistry and reaction conditions selected. Herein, we present a synthetic and computational study for this tandem process on a variety of amino ester substrates.
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