Enantiopure cis-2,5-disubstituted 2,5-dihydropyrroles from D-glycal-derived vinyl aziridines.
Upon treatment with the K- and Li-enolates of a methylene active compound, such as dimethyl malonate and dibenzoylmethane, D-allal- and D-galactal-derived vinyl N-mesyl aziridines are stereoselectively transformed, in a unique step, into diastereoisomeric, highly functionalized, enantiopure cis-2,5-disubstituted N-mesyl-2,5-dihydropyrroles.
Dipartimento di Farmacia, Via Bonanno 33 and Dipartimento di Chimica e Chimica Industriale, via Risorgimento 35, Università di Pisa , 56126 Pisa, Italy.
Valeria
V
Di Bussolo
Ileana
I
Frau
Stefano
S
Crotti
Gloria
G
Uccello-Barretta
Federica
F
Balzano
Mauro
M
Pineschi
Paolo
P
Crotti
D001388:Aziridines / Q000737:chemistry*; D003500:Cyclization; D005690:Galactose / Q000031:analogs & derivatives / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001388:Aziridines; D011758:Pyrroles; C002038:galactal; D005690:Galactose