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

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Catalytic Asymmetric Diels–Alder Reaction/[3,3] Sigmatropic Rearrangement Cascade of 1‐Thiocyanatobutadienes
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2018-06-19 , DOI: 10.1002/anie.201804811
Yuhang Zhou ₁ , Lili Lin ₁ , Xiaohua Liu ₁ , Xinyue Hu ₁ , Yan Lu ₁ , Xiying Zhang ₁ , Xiaoming Feng _{1,

2}

Affiliation

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.

中文翻译：

催化不对称Diels–Alder反应/ [1-硫氰酸根合丁二烯的[3,3]σ重排级联

通过使用手性N，N'-二氧化物/镍（II）配合物实现了亚甲基吲哚酮与1-硫氰酸根合丁二烯的高效不对称Diels-Alder / [3,3]σ重排反应。以高收率合成了一系列环己烯基异硫氰酸酯，具有出色的非对映选择性和对映选择性。基于机理研究，提出了具有可能的过渡态模型的催化循环来解释这一过程。

更新日期：2018-06-19

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