Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 136, Issue 31, Pages 11176-11181Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja506036q
Keywords
-
Categories
Funding
- NIH/NIGMS [2R01 GM 076153B]
- University of Illinois
Ask authors/readers for more resources
A Pd(II)/bis-sulfoxide/Bronsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and pi-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
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