Asymmetric synthesis of spiro[benzofuran-pyrrolidine]-indolinedione via bifunctional urea catalyzed [3 + 2]-annulation†

IF 2.9 3区 化学 Q1 CHEMISTRY, ORGANIC
Sankar Bharani , Biddika Ananda Rao , L. Raju Chowhan , Raghavaiah Pallepogu , Madavi S. Prasad
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引用次数: 0

Abstract

In this study, we unveil a highly enantioselective [3 + 2] annulation protocol, adept at merging N-2,2,2-trifluoroethylisatin ketimines with 3-alkylidene benzofuranones under quinine-derived urea catalysis. This strategy furnishes complex spiro[benzofuran-pyrrolidine]indolinedione architectures, featuring strategically positioned trifluoromethyl groups of considerable pharmacological significance. The method distinguishes itself by employing minimal catalyst loadings while ensuring energy efficiency and accommodating a broad spectrum of substrates, resulting in excellent yields and exceptional stereocontrol (38 examples, up to 98% yield, up to >20 : 1 dr, and up to 99 : 1 er). Mechanistic investigations, underpinned by SC-XRD and NMR NOE analyses, elucidate the stereochemical pathways driving selectivity, while a comprehensive evaluation of electronic and steric substituent effects further refines the reaction's scope.

Abstract Image

双功能脲催化[3 + 2]环化不对称合成螺[苯并呋喃-吡咯烷]-吲哚二酮。
在这项研究中,我们揭示了一个高度对映选择性的[3 + 2]环化方案,擅长在奎宁衍生的尿素催化下将n -2,2,2-三氟乙基化atin酮与3-烷基基苯并呋喃酮合并。该策略提供了复杂的螺[苯并呋喃-吡咯烷]吲哚啉二酮结构,具有战略性定位的具有相当药理意义的三氟甲基。该方法的特点是使用最少的催化剂负载,同时确保能源效率和适应广泛的底物,从而产生优异的产率和卓越的立体控制(38个例子,产率高达98%,高达> 20:1 dr,高达99:1 er)。基于SC-XRD和NMR NOE分析的机理研究阐明了驱动选择性的立体化学途径,而电子和立体取代基效应的综合评价进一步细化了反应的范围。
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来源期刊
Organic & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
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