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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201804811
Subject(s) - sigmatropic reaction , catalysis , chemistry , catalytic cycle , diels–alder reaction , cope rearrangement , cascade , rearrangement reaction , organic chemistry , combinatorial 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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