Asymmetric Biomimetic Aldol Reaction of Glycinate with Aliphatic Aldehydes for Efficient Synthesis of Chiral β-Hydroxy-α-Amino Acid Esters

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-07-29 DOI:10.1039/d5qo00653h

Tao Liu, Dong Ma, Mingming Lu, Ting Ma, Siqi Liu, Guoqing Zhao, Baoguo Zhao

引用次数: 0

Abstract

In biological systems, enzyme catalyzed processes are efficient and environmentally friendly ways for the transformations of various substances. Biomimetic processes can provide straight forward strategies for the synthesis of target molecules. Asymmetric biomimetic aldol reaction of glycinate is a highly efficient method for the synthesis of chemically and biologically important chiral β-hydroxy-α-amino acid esters. Herein, we developed an asymmetric aldol reaction of glycinate with aliphatic aldehydes using chiral N-quaternized pyridoxal as catalyst, affording a variety of chiral β-hydroxy-α-amino acid esters in 20–91% yields, with up to > 20:1 dr and up to 99% ee.

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甘氨酸与脂肪醛不对称仿生醛醇反应高效合成手性β-羟基-α-氨基酸酯

在生物系统中，酶催化过程是各种物质转化的高效和环保的方式。仿生过程可以为目标分子的合成提供直接的策略。甘氨酸不对称仿生醛醇反应是合成具有重要化学和生物学意义的手性β-羟基-α-氨基酸酯的高效方法。本研究以手性n季铵化吡哆醛为催化剂，建立了甘氨酸与脂肪醛的不对称醛醇反应，得到了多种手性β-羟基-α-氨基酸酯，产率为20-91%，收率高达>；[20:1]和高达99%的ee。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.