An unexpected photoinduced cyclization to synthesize fully substituted γ-spirolactones via intramolecular hydrogen abstraction with allyl acrylates. Issue 9 (1st March 2022)

• Record Type: Journal Article
• Authors: Sun, Xin; Zhou, Min; Zhu, Jing-Ping; Zhang, Xiang-Fei; Liu, Zu-Jiang; Li, Hao-Ran; Chen, Yan; Chen, He-Ping; Zhao, Jie; Pu, Jian-Xin; Yu, Miao; Liu, Ji-Kai; Wu, Bin
• Is Part Of: Organic chemistry frontiers. Volume 9:Issue 9(2022)
• Page Start: 2316
• Page End: 2321
• Publication Date: 2022-03-01
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d1qo01952j
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A photoinduced intramolecular cyclization of allyl acrylates to synthesize fully substituted spiro-γ-butyrolactone compounds is described. The reaction is believed to proceed through an intramolecular hydrogen abstraction strategy. Abstract : A photoinduced intramolecular cyclization of allyl acrylates to synthesize fully substituted spiro-γ-butyrolactone compounds is described. The reaction is believed to proceed through activation of the carbonyl group upon ultraviolet irradiation, 1, 4-hydrogen atom transfer, and intramolecular cyclization of diradical species, an intramolecular hydrogen abstraction strategy, based on a series of control and isotope studies as well as DFT calculations.