6533b834fe1ef96bd129df8a

RESEARCH PRODUCT

Retro-Diels-Alder Protocol for the Synthesis of Pyrrolo[1,2-a]pyrimidine and Pyrimido[2,1-a]isoindole Enantiomers

Zita TothMikko M. HänninenFerenc MiklósReijo SillanpääFerenc FülöpFerenc FülöpEnikő Forró

subject

chemistry.chemical_classificationChiral auxiliaryPyrimidineStereochemistryOrganic ChemistryDominoAmino acidchemistry.chemical_compoundMicrowave chemistrychemistryDiels alderPhysical and Theoretical ChemistryEnantiomerIsoindole

description

A simple protocol was introduced to prepare several enantiomerically pure heterocycles by using (–)-(1R,2R,3S,4S)-3-aminonorbornene-2-carboxylic acid as a chiral auxiliary. The protocol is based on a domino ring-closure reaction, in which the relative configuration of the new asymmetric center is controlled by the stereochemistry of the amino acid, followed by a microwave-induced retro-Diels–Alder reaction.

yearjournalcountryeditionlanguage
2013-06-19European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201300452