Access to P-chiral sec- and tert-phosphine oxides enabled by Le-Phos-catalyzed asymmetric kinetic resolution,Chemical Science

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Access to P-chiral sec- and tert-phosphine oxides enabled by Le-Phos-catalyzed asymmetric kinetic resolution
Chemical Science ( IF 7.6 ) Pub Date : 2020-09-02 , DOI: 10.1039/d0sc04041j
Haile Qiu _{1,

2,

3,

4} , Qiang Dai _{1,

2,

3,

4} , Jiafeng He _{1,

2,

3,

4} , Wenbo Li _{1,

2,

3,

4} , Junliang Zhang _{1,

2,

3,

4,

5}

Affiliation

The synthesis of P-stereogenic building blocks is extremely difficult. Herein we report an efficient kinetic resolution of secondary phosphine oxides via a Le-Phos-catalyzed asymmetric allylation reaction with Morita–Baylis–Hillman carbonates. This method provides facile access to enantioenriched secondary and tertiary P-chiral phosphine oxides with broad substrate scope, both of which could serve as P-stereogenic synthons, and can be rapidly incorporated into a given scaffold bearing a P-stereocenter. The highly desirable late stage modifications demonstrate the practicability of our method and can be a critical contribution to obtaining optimal P-chiral catalysts and ligands.

中文翻译：

Le-Phos催化的不对称动力学拆分可实现对位手性仲和叔膦氧化物

P-立体异构结构单元的合成非常困难。在本文中，我们报告了通过Le-Phos催化与Morita–Baylis–Hillman碳酸盐的不对称烯丙基化反应，可以有效地动力学分解次膦氧化物。该方法提供了易于获得的，具有广泛底物范围的对映体富集的对映体和对映体的P-手性膦氧化物，两者均可以用作P-立体异构合成子，并且可以快速地掺入具有P-立体中心的给定支架中。高度期望的后期修饰证明了我们方法的实用性，并且可能对获得最佳的P-手性催化剂和配体起关键作用。

更新日期：2020-09-23

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