Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 26, Pages 8092-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja072793w
Keywords
-
Categories
Ask authors/readers for more resources
The copper-catalyzed intramolecular O-vinylation of gamma-bromohomoallylic alcohols was investigated. With 10 mol % of CuI as the catalyst and 20 mol % of 1,10-phenanthroline as the ligand, the reactions of 3-bromo-3-buten-1-ols in refluxing CH3CN led to the convenient formation of the corresponding 2-methyleneoxetanes in good to excellent yields via a 4-exo ring closure. The configuration of the CC bond was nicely retained. This methodology was then successfully extended to the cyclization in 5-exo, 6-exo, and even 6-endo modes. Moreover, the competition experiments revealed that 4-exo cyclization is fundamentally preferred over other modes of cyclization. On the other hand, the corresponding Pd(0)-catalyzed O-vinylation showed the predominance of 5-exo over 4-exo 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