Kinetic Resolution of α‐Allyl‐α‐cinnamyl Carboxylic Acids Bearing an All‐Carbon Quaternary Stereocenter via Bromolactonization Catalyzed by a Chiral Bifunctional Sulfide

IF 2.8 4区 化学 Q1 CHEMISTRY, ORGANIC Asian Journal of Organic Chemistry Pub Date : 2024-09-12 DOI:10.1002/ajoc.202400405
Ken Okuno, Sao Sumida, Seiji Shirakawa
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Abstract

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.
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通过手性双官能团硫化物催化的溴化内酯化作用,动力学解析带有全碳季立体中心的 α-烯丙基-α-肉桂酰基羧酸
外消旋羧酸的催化动力学解析是制备光学活性手性羧酸的重要方法。虽然已经报道了几种有效的催化动力学解析手性 α-叔羧酸的方法,但高效动力学解析 α-季羧酸仍然是一项重大挑战。在此背景下,我们旨在开发α-季羧酸的动力学解析方法。我们的方法涉及一种由 BINOL 衍生的手性双功能硫化物催化溴内酯化技术,该技术由我们的研究小组开发。在这项工作中,我们报告了通过化学和立体选择性溴化内酯化,对带有 α 季立体中心的 α-allyl-α-cinnamyl 羧酸的动力学解析。使用 BINOL 衍生的带有羟基的手性双官能团硫化物催化剂是高效动力学解析外消旋 α-烯丙基-α-肉桂基羧酸的关键。
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来源期刊
CiteScore
4.70
自引率
3.70%
发文量
372
期刊介绍: Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC) The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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