Design and Synthesis of a [2.2]Paracyclophane‐based Planar Chiral Dirhodium Catalyst and its Applications in Cyclopropanation Reaction of Vinylarenes with α‐Methyl‐α‐Diazo Esters,Advanced Synthesis & Catalysis

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Design and Synthesis of a [2.2]Paracyclophane‐based Planar Chiral Dirhodium Catalyst and its Applications in Cyclopropanation Reaction of Vinylarenes with α‐Methyl‐α‐Diazo Esters
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2020-06-25 , DOI: 10.1002/adsc.202000512
Christoph Zippel ₁ , Zahid Hassan _{1,

2} , Martin Nieger ₃ , Stefan Bräse _{1,

2,

4}

Affiliation

A planar chiral dirhodium paddlewheel complex Rh₂(S_p−PCP)₄ based on the [2.2]paracyclophane has been synthesized for the challenging cyclopropanation of venylarene derivatives with tert‐butyl α‐diazo propionates. The homobimetallic rhodium catalyst relies on the high steric demand and rigidity of [2.2]paracyclophane that favors the cyclopropanation of 1‐aryl substituted, 1,1‐disubstituted and benzannulated alkenes over β‐hydride migration at room temperature with high diastereoselectivity.

中文翻译：

[2.2]基于环芳烷的平面手性铱催化剂的设计，合成及其在乙烯基芳烃与α-甲基-α-重氮酯的环丙烷化反应中的应用

合成了一种基于[2.2]对环环糊精的平面手性ho铑配合物Rh ₂（S _p -PCP）₄，用于具有挑战性的丙烯芳烃衍生物与叔丁基α-重氮丙酸酯的环丙烷化。均双金属铑催化剂依赖于[2.2]对环环烷的高空间需求和刚性，后者在室温下具有较高的非对映选择性，有利于1-芳基取代的，1,1-二取代的和苯并环化的烯烃的环丙烷化，而不是β-氢化物的迁移。

更新日期：2020-08-19

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