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铑催化3-取代色酮的不对称转移氢化反应:通过动态动力学拆分制备对映体富集的顺式-3-(羟甲基)色满-4-醇衍生物的途径

Rh-Mediated Asymmetric-Transfer Hydrogenation of 3-Substituted Chromones: A Route to Enantioenriched cis-3-(Hydroxymethyl)chroman-4-ol Derivatives through Dynamic Kinetic Resolution.

作者信息

He Bin, Phansavath Phannarath, Ratovelomanana-Vidal Virginie

机构信息

PSL University , Chimie ParisTech, CNRS, Institute of Chemistry for Life and Health Sciences , CSB2D Team , 75005 Paris , France.

出版信息

Org Lett. 2019 May 3;21(9):3276-3280. doi: 10.1021/acs.orglett.9b01002. Epub 2019 Apr 15.

Abstract

Enantioenriched cis-3-(hydroxymethyl)chroman-4-ol derivatives were conveniently prepared by rhodium-catalyzed asymmetric transfer hydrogenation of 3-formylchromones through a dynamic kinetic resolution process. The reaction proceeded under mild conditions using a low catalyst loading and HCOH/EtN (5:2) as the hydrogen source, delivering the reduced compounds in good yields, high diastereomeric ratio (up to 98:2 dr), and excellent enantioselectivities (up to >99% ee).

摘要

通过铑催化的3-甲酰基色酮的不对称转移氢化,经由动态动力学拆分过程,可方便地制备对映体富集的顺式-3-(羟甲基)色满-4-醇衍生物。该反应在温和条件下进行,使用低催化剂负载量,以HCOH/EtN(5:2)作为氢源,以良好的产率、高非对映体比率(高达98:2 dr)和优异的对映选择性(高达>99% ee)得到还原产物。

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