A Domino Ring-Closure Followed by Retro-Diels-Alder Reaction for the Preparation of Pyrimido[2,1- a]isoindole Enantiomers.

Autor:	Fekete, Beáta, Palkó, Márta, Mándity, István, Haukka, Matti, Fülöp, Ferenc
Předmět:	BETULACEAE ALDER RACEMIZATION OPTICAL isomers CHIRALITY ENANTIOMERS
Zdroj:	European Journal of Organic Chemistry; Jul2016, Vol. 2016 Issue 21, p3519-3527, 9p
Abstrakt:	A simple method was developed to prepare pyrimido[2,1- a]isoindole derivatives by using di- endo- and di- exo-ethyl 3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate enantiomers as chiral sources. The method is based on a domino ring-closure reaction of norbornene 2-aminohydroxamic acid followed by microwave-induced retro-Diels-Alder reaction. In the case of enantiomeric starting substances, the chirality is transferred from norbornene derivatives to pyrimido[2,1- a]isoindoles. The configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy [based on 2D NOE cross-peaks and 3 JH,H coupling constants] and X-ray crystallography. [ABSTRACT FROM AUTHOR]
Databáze:	Complementary Index
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