General Access to Aminobenzyl-o-carboranes as a New Class of CarboACHTUNGTRENUNGrane Derivatives: Entry to Enantiopure Carborane–Amine Combinations

Vincent Terrasson; Jose Giner Planas; Damien Prim; Francesc Teixidor; Clara Vinas; Mark E. Light; Michael B. Hursthouse

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General Access to Aminobenzyl-o-carboranes as a New Class of CarboACHTUNGTRENUNGrane Derivatives: Entry to Enantiopure Carborane–Amine Combinations

机译：作为新型CarboACHTUNGTRENUNGrane衍生物类，可普遍获得氨基苄基邻氨基甲酸酯：进入对映纯的碳硼烷-胺组合

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摘要

The convenient synthesis of original aminobenzyl-o-carboranes,which represent a new class of nitrogenated carborane derivatives, is described. These novel compounds have been efficiently prepared starting from commercially available aromatic aldehydes and monosubstituted o-carbo-ACHTUNGTRENUNGranes via carboranyl alcohols and chlorides as intermediates. The key step of this methodology is a selective nucleophilic amination under mild conditions that allows the formation of the expected amines while limiting the partial deboronation of the carborane cluster. This general strategy has been applied to the preparation of a wide variety of aminobenzyl-o- arboranes. The extension of this pathway to the synthesis of enantiopure carborane– amine combinations is also described.

机译：描述了代表一类新的硝化碳硼烷衍生物的原始氨基苄基-o-碳烷的简便合成方法。从市场上可买到的芳族醛和单取代的邻-碳-ACHTUNGTRENUNGRANes经由碳硼烷醇和氯化物作为中间体，已经有效地制备了这些新型化合物。该方法的关键步骤是在温和条件下进行选择性亲核胺化，该胺化反应可形成预期的胺，同时限制碳硼烷簇的部分脱硼。该通用策略已应用于制备多种氨基苄基-邻-硼烷。还描述了该途径扩展到对映纯碳硼烷-胺组合的合成。

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来源
《Chemistry: A European journal》 |2009年第44期|共13页
作者
Vincent Terrasson; Jose Giner Planas; Damien Prim; Francesc Teixidor; Clara Vinas; Mark E. Light; Michael B. Hursthouse;
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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
alcohols; amination; carboranes; chlorination; enantioselectivity;

机译：醇;胺化;碳烷;氯化;对映选择性;

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1. General Access to Aminobenzyl-o-carboranes as a New Class of CarboACHTUNGTRENUNGrane Derivatives: Entry to Enantiopure Carborane–Amine Combinations [J] . Vincent Terrasson, Jose Giner Planas, Damien Prim, Chemistry: A European journal . 2009,第44期

机译：作为新型CarboACHTUNGTRENUNGrane衍生物类，可普遍获得氨基苄基邻氨基甲酸酯：进入对映纯的碳硼烷-胺组合
2. Rapid entry to enantiopure carbacepham derivatives via lewis acid promoted carbonyl-ene cyclization of 2-azetidinone-tethered alkenylaldehydes [J] . Benito Alcaide, Carmen Pardo, Carolina Rodriguez-Ranera, Organic letters . 2001,第26期

机译：通过刘易斯酸快速进入对映纯的乙二胺衍生物，促进了2-氮杂环丁酮连接的烯基醛的羰基烯环化
3. Synergistic antibacterial activity of new isomeric carborane derivatives through combination with nanoscaled titania [J] . Li S., Wu C., Zhao X., Journal of biomedical nanotechnology . 2013,第3期

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4. Student’s Access Pattems of a Moodle-based Course Management System: A Case Study of a Large Entry Level Programming Class [C] . Rongkai Shi, Vijayakumar Nanjappan, Hai-Ning Liang, IEEE International Conference on Engineering, Technology and Education . 2019

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5. Applications of enantiopure sulfinimine derived chiral amine building blocks for the asymmetric synthesis of tropane alkaloids and cyclic cis-β-amino acid derivatives [D] . Theddu, Naresh 2011

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6. Structure of a xenon derivative of Escherichia coli copper amine oxidase: confirmation of the proposed oxygen-entry pathway [O] . Pascale Pirrat, Mark A. Smith, Arwen R. Pearson, 2008

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7. Cover Feature: Easy Access to Enantiopure (S )- and (R )-Aryl Alkyl Alcohols by a Combination of Gold(III)-Catalyzed Alkyne Hydration and Enzymatic Reduction (ChemCatChem 5/2018) [O] . Patricia Schaaf, Vladimir Gojic, Thomas Bayer, 2018

机译：封面特征：通过Gold（III）的组合 - 催化炔水合和酶促减少（ChemCatchem 5/2018），易于进入对映致映的烷基醇 - 和（R）芳基烷基醇（ChemCatchem 5/2018）

General Access to Aminobenzyl-o-carboranes as a New Class of CarboACHTUNGTRENUNGrane Derivatives: Entry to Enantiopure Carborane–Amine Combinations

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