Ontology highlight
ABSTRACT:
SUBMITTER: Chennamadhavuni S
PROVIDER: S-EPMC7203762 | biostudies-literature | 2018 Dec
REPOSITORIES: biostudies-literature
The Journal of organic chemistry 20181205 24
A modular and diastereodivergent synthesis of tetrahydro-1 H-pyrrolo[1,2 d]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 diastereom ...[more]