Lewis acid-catalyzed [4 + 2] cycloaddition of donor–acceptor cyclobutanes with iminooxindoles: access to spiro[piperidine-3, 2′-oxindoles]. Issue 49 (9th November 2022)

• Record Type: Journal Article
• Authors: Chen, Zuliang; Yan, Keyi; Luo, Hui; Yan, Jun; Zeng, Yang
• Is Part Of: RSC advances. Volume 12:Issue 49(2022)
• Page Start: 32097
• Page End: 32101
• Publication Date: 2022-11-09
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d2ra04730f
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : A Lewis acid-catalyzed [4 + 2] cycloaddition reaction from D–A cyclobutanes and iminooxindoles, providing the corresponding spiro[piperidine-3, 2′-oxindoles] under mild conditions. Abstract : A new approach is described for the synthesis of spiro[piperidine-3, 2′-oxindoles] in 35–82 yields with excellent stereoselectivity via the [4 + 2] cycloaddition reaction of donor–acceptor cyclobutanes with iminooxindoles in the presence of 10–30 mol% Sc(OTf)3 at room temperature. This methodology provides great potential for building spiro-heterocycle compounds from simple building blocks.