Kinetic Resolution of α-Allyl-α-Cinnamyl Carboxylic Acids Bearing an All-Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide,Asian Journal of Organic Chemistry

当前位置： X-MOL 学术 › Asian J. Org. Chem. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Kinetic Resolution of α-Allyl-α-Cinnamyl Carboxylic Acids Bearing an All-Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide
Asian Journal of Organic Chemistry ( IF 2.8 ) Pub Date : 2024-09-11 , DOI: 10.1002/ajoc.202400405
Ken Okuno ₁ , Sao Sumida ₁ , Seiji Shirakawa ₁

Affiliation

Catalytic kinetic resolutions of racemic carboxylic acids are important methods for preparing chiral carboxylic acids in their optically active forms. While several effective methods for the catalytic kinetic resolution of chiral α-tertiary carboxylic acids have been reported, the efficient kinetic resolution of α-quaternary carboxylic acids remains a significant challenge. In this context, we aimed to develop methods for the kinetic resolution of α-quaternary carboxylic acids. Our approach involves a BINOL-derived chiral bifunctional sulfide-catalyzed bromolactonization technique, which was developed by our research group. In this work, we report the kinetic resolution of α-allyl-α-cinnamyl carboxylic acids bearing an α-quaternary stereocenter via chemo- and stereoselective bromolactonizations. The use of a BINOL-derived chiral bifunctional sulfide catalyst with a hydroxy group was key for the efficient kinetic resolution of racemic α-allyl-α-cinnamyl carboxylic acids.

中文翻译：

通过手性双官能硫化物催化的溴内酯化，对带有全碳季铵立体中心的 α-烯丙基-α-肉桂基羧酸进行动力学分离

外消旋羧酸的催化动力学分离是制备光学活性形式的手性羧酸的重要方法。虽然已经报道了几种用于手性 α-叔羧酸催化动力学分离的有效方法，但 α-季铵盐羧酸的有效动力学分离仍然是一个重大挑战。在此背景下，我们的目标是开发 α-季铵盐羧酸的动力学分离方法。我们的方法涉及一种 BINO 衍生的手性双功能硫化物催化的溴化反应器化技术，该技术由我们的研究小组开发。在这项工作中，我们报道了通过化学选择性和立体选择性溴化作用α-烯丙基-α-肉桂基羧酸具有 α-四元立体中心的动力学分离。使用具有羟基的 BINO 衍生的手性双功能硫化物催化剂是外消旋 α-烯丙基-α-肉桂基羧酸高效动力学分离的关键。

更新日期：2024-09-11

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南