Manganese(iii)-promoted highly stereoselective phosphorylation of acyclic tertiary enamides to synthesize E-selective β-phosphoryl enamides. Issue 28 (6th July 2022)

• Record Type: Journal Article
• Authors: Xu, Xin-Ming; Li, Wenzhong; Li, Qiwei; Chen, Sen; Zhang, Xuesi; Yang, Bin; Wang, Wei-Li
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 28(2022)
• Page Start: 5566
• Page End: 5574
• Publication Date: 2022-07-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob00980c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A concise manganese(iii )-promoted stereoselective β-phosphorylation of tertiary enamides and diverse H-phosphine oxides was achieved, which proceeds with absolute E -selectivity in high efficiency and is the first case of E -selective β-phosphorylation of tertiary enamides. Abstract : A concise manganese(iii )-promoted stereoselective β-phosphorylation of acyclic tertiary enamides and diverse H-phosphine oxides was achieved. This reaction proceeds with absolute E -selectivity in contrast to Z -selectivity obtained in other previous works and affords various E -selective β-phosphorylated tertiary enamides in high efficiency. To the best of our knowledge, this is the first case of E -selective β-phosphorylation of tertiary enamides through C–H functionalization. In addition, the method features broad substrate scope, good functional group compatibility and efficient scale-up.