New regiocontrolled synthesis of functionalized pyrroles from 2-azetidinone-tethered allenols.
A new one-pot approach to synthesize densely substituted racemic and enantiopure pyrroles from beta-lactams has been developed. The approach relies on the regiocontrolled cyclization of beta-allenamine intermediates derived from the ring opening of 2-azetidinone-tethered allenols. In this approach four points of diversity are introduced, one of which is the position of the allene moiety on the beta-lactam ring.
Alcaide
Benito
B
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain. alcaideb@quim.ucm.es
Almendros
Pedro
P
Carrascosa
Rocío
R
Redondo
María C
MC
D000438:Alcohols / Q000737:chemistry*; D001384:Azetidines / Q000737:chemistry*; D003500:Cyclization; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C116379:2-azetidinone; D000438:Alcohols; D001384:Azetidines; D011758:Pyrroles