Journal
ORGANIC LETTERS
Volume 23, Issue 9, Pages 3729-3734Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01125
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Funding
- National Institute of General Medical Sciences [R01GM101389]
- National Institutes of Health [S10 OD021758-01A1]
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Polycyclic lactams are prepared in a single operation from otoluamides and cyclic amines, utilizing transient cyclic imines generated in situ from lithium amides and simple ketone oxidants. The annulation process involves imines like 1-pyrroline and 1-piperideine engaging lithiated o-toluamides, with undesired side reactions suppressed through careful selection of reaction conditions.
Polycyclic lactams are prepared in a single operation from otoluamides 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.
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