Journal
ORGANIC LETTERS
Volume 21, Issue 13, Pages 5073-5077Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01664
Keywords
-
Categories
Funding
- National Science Foundation [CHE-1764309-0, CHE-1414298]
- NSF [CHE-0840444]
- Basque Government Fellowship (Spain)
- Fudan University Overseas Summer Research Foundation
Ask authors/readers for more resources
The organocatalytic synthesis of densely substituted mono- and bis-gamma-lactams involving the Mukaiyama Mannich addition of 2,5-bis(trimethylsilyloxy)furan to imines is described. Use of a ditoluenesulfonylimide catalyst produces gamma-lactams from monoaddition, whereas a more acidic catalyst (triflic acid) produces fused bis-lactams from double addition. Optimized organocatalytic conditions allow for the selective synthesis of either desired core as well as the one-pot, multicomponent assembly of the trisubstituted monolactams from aldehydes, amines, and bis-trimethylsilyloxyfuran. An examination of chiral acids found these organocatalysts to be highly active and diastereoselective in the monoaddition reaction, albeit with no enantioselectivity.
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