保护环丙烷氨基酸构建块的模块化和可扩展路线

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-24 DOI:10.1021/acs.orglett.5c01341

Charlie T. Swan, Alex G. Edmonds, Stephen P. Argent, Nicholas J. Mitchell

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引用次数: 0

摘要

本文描述了一种从普通实验室试剂合成非规范环丙烷氨基酸的改进方法，避免了使用神经毒性氧化剂或贵金属催化剂。分子内异氰酸酯捕获通过霍夫曼重排允许双环氨基甲酸酯以对映体富集和非对映的方式合成。这些物种随后的开环允许获得环丙烷氨基酸，这些氨基酸可以通过氧化和SN2途径进一步功能化，并通过固相肽合成纳入肽中。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks

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A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks

An improved method for the synthesis of noncanonical cyclopropane amino acids from common laboratory reagents is described, avoiding the use of neurotoxic oxidants or precious metal catalysts. Intramolecular isocyanate trapping via a Hofmann rearrangement permits the synthesis of bicyclic carbamates in an enantioenriched and diastereopure manner. Subsequent ring-opening of these species allows access to cyclopropane amino acids which can be further functionalized via oxidation and S_N2 pathways and incorporated into peptides via solid-phase peptide synthesis.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.