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Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones via a One-Pot Intramolecular aza-Michael/Lactamization Sequence
journal contribution
posted on 2018-11-20, 00:00 authored by Spandan Chennamadhavuni, James S. Panek, John A. Porco, Lauren E. BrownA 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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Chiral Tetrahydropyrrolodiazepinedionesestersdiastereodivergent synthesisreaction conditionsHereinester substratesinterplayvarietybase-mediatedmaterial stereochemistrypropensityDiastereodivergent Synthesisacid-coupled homoallylicdiastereomerisomerizationchiral centersepimerizationSequenceOne-Pot Intramolecular azaDiastereoselectivitytandem processtetrahydropyrrolodiazepinedione scaffoldcyclization event
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