Open Accessα-C–H/N–H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams
Author(s) -
Weijie Chen,
Daniel Seidel
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01125
Subject(s) - annulation , chemistry , deprotonation , alicyclic compound , imine , ketone , lithium (medication) , combinatorial chemistry , medicinal chemistry , organic chemistry , catalysis , ion , medicine , endocrinology
Polycyclic lactams are prepared in a single operation from o -toluamides and cyclic amines in a process that involves transient cyclic imines, species that are conveniently obtained in situ from the corresponding lithium amides and simple ketone oxidants. Imines thus generated, such as 1-pyrroline and 1-piperideine, engage lithiated o -toluamides in a facile annulation process. Undesired side reactions such as imine deprotonation and o -toluamide dimerization are suppressed through the judicious choice of reaction conditions.