Synthesis of polysubstituted azetidines via cascade trifluoromethylation/cyclization of N-allyl ynamides
Literature Information
Publication Date
2021-06-14
DOI
10.1039/D1QO00559F
Impact Factor
5.281
Authors
Genlai Zhou, Jingwen Su, Tianbo Shang, Xiaojuan Wang, Yihui Bai, Zheliang Yuan, Gangguo Zhu
View Original
Abstract
Traditional methods for the transformation of N-allyl ynamides rely on the formation of a ketenimine intermediate or its equivalent, while novel reaction modes remain to be developed. Herein, a cascade trifluoromethylation/cyclization of N-allyl sulfonylynamides is realized, which provides a facile access to azetidine-fused tricyclic compounds under very mild reaction conditions. It represents a rare example of 4-exo-dig radical cyclization, thus opening up a new opportunity for constructing synthetically attractive azetidines from the readily available N-allyl ynamides.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
3-(3-Ethyl-1-methyl-3-azepanyl)phenol hydrochloride (1:1)
CAS Number:
59263-76-2
Molecular Formula:
C15H24ClNO
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