Merging Au(I)-Catalysis and Biocatalysis: Practical and Scalable Synthesis of Chiral Amino Building Blocks from Alkynes

IF 13.1 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-01-27 DOI:10.1021/acscatal.4c0725910.1021/acscatal.4c07259

Meriem Daghmoum, Nazarii Sabat, Meije Lecoq, Thelma Viraize and Xavier Guinchard*,

引用次数: 0

Abstract

Au(I)-catalyzed hydration of aliphatic terminal alkynes is followed by transaminase-catalyzed reductive amination, leading to enantioenriched chiral amines. The approach features a one-pot reaction with no particular need for a compartmentalization strategy. Final functionalization performed in situ leads to a variety of chiral amines, pyrroles, and 1-pyrrolines obtained in high enantioselectivities. The method demonstrates applicability to the synthesis of bioactive drugs such as clobenzorex (43% yield, 3 steps, 96% ee) and a precursor of lisdexamfetamine (34% yield, 3 steps, dr 98:2).

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合并Au(I)-催化和生物催化：炔手性氨基构建块的实用和可扩展合成

金(I)催化的脂肪末端炔的水化反应，接着是转氨酶催化的还原性胺化反应，生成对映体富集的手性胺。这种方法的特点是一锅反应，不需要特别的分区策略。在原位进行的最终功能化导致获得高对映选择性的各种手性胺，吡咯和1-吡咯。结果表明，该方法适用于合成氯苯甲氧胺（收率43%，3步，ee 96%）和利地塞米明前体（收率34%，3步，dr 98:2）等生物活性药物。

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

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.