A detailed investigation of the aza-Prins reaction.
The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s).
Dobbs
Adrian P
AP
School of Biological and Chemical Sciences, Joseph Priestley Building, Queen Mary University of London, Mile End Road, London, United Kingdom E1 4NS. A.Dobbs@qmul.ac.uk
Guesné
Sebastien J J
SJ
Parker
Robert J
RJ
Skidmore
John
J
Stephenson
Richard A
RA
Hursthouse
Mike B
MB
D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D010880:Piperidines; D011759:Pyrrolidines