Catalytic Asymmetric Diels–Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1‐Thiocyanatobutadienes | Zendy

Zhou Yuhang | Zendy; Lin Lili | Zendy; Liu Xiaohua | Zendy; Hu Xinyue | Zendy; Lu Yan | Zendy; Zhang Xiying | Zendy; Feng Xiaoming | Zendy

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Catalytic Asymmetric Diels–Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1‐Thiocyanatobutadienes

Author(s) -

Zhou Yuhang,

Lin Lili,

Liu Xiaohua,

Hu Xinyue,

Lu Yan,

Zhang Xiying,

Feng Xiaoming

Publication year - 2018

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201804811

Subject(s) - sigmatropic reaction , catalysis , chemistry , cascade , catalytic cycle , diels–alder reaction , cope rearrangement , combinatorial chemistry , medicinal chemistry , organic chemistry , chromatography

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.

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