Reactions of N-alkyl-2,3-dihydro-4-pyridones and 4-(pyrrolidin-1-yl)furan-2(5H)-one with aldehydes and triethylsilane in a one-flask procedure provided C5 and C3 alkylated derivatives, respectively. Mannich-type reactions with formaldehyde and carbamates in the presence of lithium perchlorate furnished C5/C3 methylcarbamates.
Bibliographical noteFunding Information:
We gratefully acknowledge financial support from the National Institutes of Health Grant GM081267 and the University of Minnesota through the Vince and McKnight Endowed Chairs. We thank Erick Carlson for his assistance with the assembly of the supplementary data.
© 2015 The Authors.
- Mannich reaction
- Regioselective alkylation