Switchable multipath cascade cyclization to synthesize bicyclic lactams and succinimides via chemodivergent reaction. Issue 22 (28th February 2023)

• Record Type: Journal Article
• Authors: Song, Yimei; Wu, Chaofei; Zhang, Jinhai; Zhang, Wenhai; Qin, Xin; Yang, Yixiao; Kang, Guowei; Jiang, Jun; Liu, Hongxin
• Is Part Of: Chemical communications. Volume 59:Issue 22(2023)
• Page Start: 3313
• Page End: 3316
• Publication Date: 2023-02-28
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/d2cc06841a
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Herein, a novel chemodivergent reaction of switchable multipath cascade cyclization was developed to efficiently synthesize γ-lactone fused γ-lactams and succinimide fused hemiketals. Abstract : Herein, a novel switchable multipath cascade cyclization via chemodivergent reaction between readily available ketoamides and deconjugated butenolides was developed to efficiently synthesize γ-lactone fused γ-lactams and succinimide fused hemiketals. The Aldol/aza-Michael reaction and Aldol/imidation/hemiketalization reaction were enabled by catalytic amounts of two bases, namely tetramethyl guanidine and NaOAc. A wide range of substrate scope with diverse functional group compatibility was demonstrated to deliver the corresponding products with good yield and excellent diastereoselectivity (>60 examples).