10.1021/acs.joc.8b02724.s001
Spandan Chennamadhavuni
Spandan
Chennamadhavuni
James S. Panek
James S.
Panek
John A. Porco
John A.
Porco
Lauren E. Brown
Lauren E.
Brown
Diastereodivergent Synthesis of Chiral Tetrahydropyrrolodiazepinediones
via a One-Pot Intramolecular <i>aza</i>-Michael/Lactamization
Sequence
American Chemical Society
2018
Chiral Tetrahydropyrrolodiazepinediones
esters
diastereodivergent synthesis
reaction conditions
Herein
ester substrates
interplay
variety
base-mediated
material stereochemistry
propensity
Diastereodivergent Synthesis
acid-coupled homoallylic
diastereomer
isomerization
chiral centers
epimerization
Sequence
One-Pot Intramolecular aza
Diastereoselectivity
tandem process
tetrahydropyrrolodiazepinedione scaffold
cyclization event
2018-11-20 00:00:00
Journal contribution
https://acs.figshare.com/articles/journal_contribution/Diastereodivergent_Synthesis_of_Chiral_Tetrahydropyrrolodiazepinediones_via_a_One-Pot_Intramolecular_i_aza_i_-Michael_Lactamization_Sequence/7427489
A modular
and diastereodivergent synthesis of tetrahydro-1<i>H</i>-pyrrolo[1,2<i>d</i>]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.