Journal
ORGANIC LETTERS
Volume 20, Issue 17, Pages 5384-5388Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02301
Keywords
-
Categories
Funding
- National Science Foundation [NSF-1566402]
Ask authors/readers for more resources
Reported herein is the development of [3 + 3] cycloaddition reactions between oxyallyl cations and nitrones to yield 1,2-oxazinane heterocycles. Oxyallyl cation intermediates, generated in situ from alpha-tosyloxy ketones in the presence of hexafluoro-2-propanol (HFIP), a cosolvent, and a base, are found to react with a range of nitrones to afford 1,2-oxazinanes in good to high yields. The reactions are catalyzed by hydrogen-bond donors such as phenols and squaramides, and dramatically higher diastereoselectivities are observed with 4-nitrophenol.
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