Synthesis of polysubstituted azetidines via cascade trifluoromethylation/cyclization of N-allyl ynamides. Issue 16 (17th June 2021)

• Record Type: Journal Article
• Authors: Zhou, Genlai; Su, Jingwen; Shang, Tianbo; Wang, Xiaojuan; Bai, Yihui; Yuan, Zheliang; Zhu, Gangguo
• Is Part Of: Organic chemistry frontiers. Volume 8:Issue 16(2021)
• Page Start: 4473
• Page End: 4478
• Publication Date: 2021-06-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo00559f
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A cascade trifluoromethylation/cyclization of N -allyl sulfonylynamides is developed, providing a direct access to azetidine-fused tricyclic compounds at room temperature. 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.