Cascade dearomative [4 + 2] cycloaddition of indoles with in situ generated ortho-quinone methides: practical access to divergent indoline-fused polycycles. Issue 9 (19th April 2022)

• Record Type: Journal Article
• Authors: Dong, Pei-Zhen; Qiu, Bin; An, Xiao-De; Xiao, Jian
• Is Part Of: Green chemistry. Volume 24:Issue 9(2022)
• Page Start: 3772
• Page End: 3777
• Publication Date: 2022-04-19
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/d2gc00387b
• Languages: English
• ISSNs: 1463-9262

Abstract

Abstract : A rationally designed cascade dearomative [4 + 2] cycloaddition of indoles with in situ generated o -QM has been developed to assemble indoline-fused polycycles divergently with high yields and excellent diastereoselectivity in one step. Abstract : A rationally designed cascade dearomative [4 + 2] cycloaddition of indoles with in situ generated ortho -quinone methide ( o -QM) provides a practical, atom and step economical access to diverse indoline-fused polycycles with high yields and excellent diastereoselectivity in one step. These polycyclic indolines feature divergent [6–6–5] and [6–5–5] tricyclic core skeletons bearing three contiguous stereogenic centers. Appealingly, most of the products precipitating in ethanol solution, the use of room temperature, easy handling, broad substrate scope and gram-scale synthesis make this transformation an environmentally benign, effective and attractive method for the synthesis of polycyclic indolines.