通过 N-1-(1-萘基)乙基取代基和 BINAM 衍生的双脲类有机催化剂控制 2-EWG 取代的氮杂环丁烷盐与氟化物发生亲核开环反应的位置

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC Tetrahedron Pub Date : 2024-09-14 DOI:10.1016/j.tet.2024.134274
Eiji Tayama , Ryoga Tsutsumi , Daisuke Uraguchi
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引用次数: 0

摘要

BINAM(1,1′-联萘-2、室温下,在二氯甲烷中用氟化铯催化具有光学活性和非对映纯度的 2-EWG(电子抽取基)取代的 N-(1-(1-萘基)乙基)氮杂环丁烷盐的双脲催化亲核开环反应,在立体阻碍较小的 4 位进行,而在电子缺陷较小的 2 位进行。通过结合手性立体中心(如 N-(1-(1-萘基)乙基)氮杂环丁烷盐)和手性双脲催化剂的立体体积,可实现 4 位的选择性开环。反应生成非对映纯的γ-氟-α-氨基丁酸衍生物。该方案适用于从市售的手性 1-(1-萘基)乙胺开始合成对映体富集(98 % ee)的γ-氟-α-氨基酸衍生物。
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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Controlling the position of the nucleophilic ring-opening of 2-EWG-substituted azetidinium salts with fluoride by the N-1-(1-naphthyl)ethyl substituent and BINAM-derived bis-urea organocatalyst

BINAM (1,1′-binaphthyl-2,2′-diamine)-derived bis-urea-catalyzed nucleophilic ring-opening of optically active and diastereomerically pure 2-EWG (electron-withdrawing group)-substituted N-(1-(1-naphthyl)ethyl)azetidinium salts with cesium fluoride in dichloromethane at room temperature proceeds at the less sterically hindered 4-position over the electronically deficient 2-position. Selective ring-opening at the 4-position is achieved by the combination of chiral stereocenters, as in N-(1-(1-naphthyl)ethyl)azetidinium salt, and steric bulk of the chiral bis-urea catalysts. The reaction affords the corresponding γ-fluoro-α-aminobutyric acid derivatives in diastereomerically pure. This protocol is applicable to the synthesis of enantiomerically enriched (98 % ee) γ-fluoro-α-amino acid derivatives starting from the commercially available chiral 1-(1-naphthyl)ethylamine.

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来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
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