Asymmetric Enamide–Imine Tautomerism in the Kinetic Resolution of Tertiary Alcohols,Angewandte Chemie International Edition

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Asymmetric Enamide–Imine Tautomerism in the Kinetic Resolution of Tertiary Alcohols
Angewandte Chemie International Edition ( IF 16.1 ) Pub Date : 2021-07-27 , DOI: 10.1002/anie.202106151
Mengyao Tang _{1,

2,

3} , Huanchao Gu ₁ , Shunlong He ₁ , Subramani Rajkumar ₁ , Xiaoyu Yang ₁

Affiliation

An efficient protocol for kinetic resolution of tertiary alcohols has been developed through an unprecedented asymmetric enamide-imine tautomerism process enabled by chiral phosphoric acid catalysis. A broad range of racemic 2-arylsulfonamido tertiary allyl alcohols could be kinetically resolved with excellent kinetic resolution performances (with s-factor up to >200). This method is particularly effective for a series of 1,1-dialkyl substituted allyl alcohols, which produced chiral tertiary alcohols that would be difficult to access via other asymmetric methods. Facile and versatile transformations of the chiral α-hydroxy imine and enamide products, especially the efficient stereodivergent synthesis of all four stereoisomers of β-amino tertiary alcohols using one enantiomer of the catalyst, demonstrated the value of this kinetic resolution method.

中文翻译：

叔醇动力学拆分中的不对称烯酰胺-亚胺互变异构现象

通过手性磷酸催化实现前所未有的不对称烯酰胺-亚胺互变异构过程，开发了一种有效的叔醇动力学拆分方案。广泛的外消旋 2-芳基磺酰氨基叔烯丙醇可以以优异的动力学拆分性能进行动力学拆分（具有s- 系数高达 >200）。这种方法对一系列 1,1-二烷基取代的烯丙醇特别有效，这些烯丙醇产生了难以通过其他不对称方法获得的手性叔醇。手性 α-羟基亚胺和烯酰胺产物的简便和通用转化，特别是使用催化剂的一种对映体对 β-氨基叔醇的所有四种立体异构体进行有效的立体发散合成，证明了这种动力学拆分方法的价值。

更新日期：2021-09-14

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