Catalytic Asymmetric Diels–Alder Reaction/[3, 3] Sigmatropic Rearrangement Cascade of 1‐Thiocyanatobutadienes. (19th June 2018)

• Record Type: Journal Article
• Authors: Zhou, Yuhang; Lin, Lili; Liu, Xiaohua; Hu, Xinyue; Lu, Yan; Zhang, Xiying; Feng, Xiaoming
• Is Part Of: Angewandte Chemie. Volume 130:Number 29(2018)
• Page Start: 9251
• Page End: 9254
• Publication Date: 2018-06-19
• Subjects: Asymmetrische Katalyse -- Cycloadditionen -- Isothiocyanate -- Nickel -- Umlagerungen; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201804811
• Languages: English
• ISSNs: 0044-8249

Abstract

Abstract: A highly efficient asymmetric Diels–Alder/[3, 3] sigmatropic rearrangement reaction of methyleneindolinones with 1‐thiocyanatobutadienes has been realized by using a chiral N, N ′‐dioxide/nickel(II) complex as the catalyst. A range of cyclohexenyl isothiocyanates were synthesized in high yields with excellent diastereo‐ and enantioselectivities. Based on mechanistic studies, a catalytic cycle with possible transition‐state models were proposed to explain the process.