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Access to Optically Active 3‐Aminopiperidines by Ring Expansion of Prolinols: Thermodynamic versus Kinetic Control
Author(s) -
Cochi Anne,
Pardo Domingo Gomez,
Cossy Janine
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101829
Subject(s) - chemistry , pyrrolidine , azide , ring (chemistry) , kinetic control , kinetic energy , tetrafluoroborate , pyrroline , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , physics , ionic liquid , quantum mechanics
3‐Aminopiperidines are of great interest because they can possess a wide range of biological activity depending on the nitrogen substituents. Different approaches their synthesis are presented and the most efficient is a ring expansion of prolinols induced by XtalFluor‐E (diethylaminodifluorosulfinium tetrafluoroborate) in the presence of tetrabutylammonium azide, via an aziridinium intermediate, followed by the reduction of the corresponding azide. Under kinetic conditions, a 2‐(azidomethyl)pyrrolidine/3‐azidopiperidine ratio of 0:100 can be attained depending on the substituents present on the prolinol.