A regio- and diastereoselective intramolecular nitrone cycloaddition for practical 3- and 2,3-disubstituted piperidine synthesis from gamma-butyrolactone.
A fast and efficient route for diversity-oriented synthesis of 3- and 2,3-disubstituted piperidines, featuring an intramolecular nitrone cycloaddition with high regio- and diastereoselectivity, was achieved in six steps and 36-66% overall yield from commercially available gamma-butyrolactone or 1,4-butanediol. A new N-alkenyl nitrone enoate was used in this intramolecular nitrone cycloaddition, and the regioselectivity, diastereoselectivity, and reversibility of this cycloaddition were investigated.
Stephens
Benjamin E
BE
Department of Chemistry & Biomolecular Sciences, Macquarie University, Sydney, NSW 2109, Australia.
Liu
Fei
F
D015107:4-Butyrolactone / Q000737:chemistry*; D003500:Cyclization; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009589:Nitrogen Oxides; D010880:Piperidines; C015388:nitrones; D015107:4-Butyrolactone