Catalytic Asymmetric Diels–Alder Reaction/[3, 3] Sigmatropic Rearrangement Cascade of 1‐Thiocyanatobutadienes. Issue 29 (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 international edition. Volume 57:Issue 29(2018)
• Page Start: 9113
• Page End: 9116
• Publication Date: 2018-06-19
• Subjects: asymmetric catalysis -- cycloaddition -- isothiocyanates -- nickel -- rearrangements; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201804811
• Languages: English
• ISSNs: 1433-7851

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. Abstract : ′Nickel′ for your thoughts : A highly efficient asymmetric Diels–Alder/[3, 3] sigmatropic rearrangement reaction of methyleneindolinones with 1‐thiocyanatobutadienes was realized by using a chiral N, N ′‐dioxide/nickel(II) complex as the catalyst. A range of cyclohexenyl isothiocyanates were synthesized in high yields and with excellent diastereo‐ and enantioselectivities. Pg=protecting group.