Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 9, Pages 6518-6527Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00352
Keywords
-
Categories
Funding
- Department of Science and Technology-Science and Engineering Research Board (DST-SERB), New Delhi, India [EMR/2017/002298, IICT/Pubs/2021/086]
- CSIR, New Delhi, India
- UGC, New Delhi, India
Ask authors/readers for more resources
This manuscript describes a convenient, mild, and highly stereoselective method for the allylation of delta-hydroxy-alpha,beta-unsaturated ketones using allyltrimethylsilane mediated by BF3 center dot OEt2, resulting in 2,4-diallyl-2-methyl-6-aryltetrahydro-2H-pyran ring systems with quaternary carbon stereogenic centers. The isolation of TMS-protected lactol as an intermediate strongly supports the proposed mechanistic pathway.
The present manuscript describes a convenient, mild, and highly stereoselective method for the allylation of delta-hydroxy-alpha,beta-unsaturated ketones having a benzylic hydroxyl group at the delta-position using allyltrimethylsilane mediated by BF3 center dot OEt2, leading to 2,4-diallyl-2-methyl-6-aryltetrahydro-2H-pyran ring systems with quaternary carbon stereogenic centers. This represents the first example of a tandem isomerization followed by one C-O and two C-C bond-forming reactions in one pot. The isolation of TMS-protected lactol as an intermediate from the reaction strongly supports the proposed mechanistic pathway.
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