Journal
SYNLETT
Volume 30, Issue 4, Pages 464-470Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0037-1611670
Keywords
SnAP reagents; N-heterocycles; morpholines; cyclization; radical clock; mechanism
Categories
Funding
- European Research Council (ERC) [306793-CASAA]
Ask authors/readers for more resources
Saturated nitrogen heterocycles can be found with increasing abundance in bioactive molecules despite a limited number of methods to access these scaffolds. However, the coupling of recently introduced SnAP [tin (Sn) amine protocol] reagents with a wide range of aldehydes and ketones has proven to be a reliable, practical, and versatile one-step approach to saturated N-heterocycles. While effective, the lack of mechanistic understanding limits efforts to develop new catalytic and enantioselective variants. To distinguish between a polar or radical mechanism, we assessed Lewis and BrOnsted acids, radical trapping experiments, and radical clock SnAP reagents reinforcing the current understanding of the SnAP protocol as a radical cyclization.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available