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Preparation and Applications of 4-Methoxybenzyl Esters in Organic Synthesis
Organic Preparations and Procedures International ( IF 1.2 ) Pub Date : 2016-01-02 , DOI: 10.1080/00304948.2016.1127096
Kyle T Howard 1 , John D Chisholm 1
Affiliation  

Introduction .............................................................................................. 2 I. Formation of PMB Esters ........................................................................... 3 1. From Carboxylic Acids......................................................................... 3 2. From Activated Esters .......................................................................... 8 3. From Other Esters and Imides ................................................................ 9 4. From Aldehydes ................................................................................ 12 II. Deprotection of PMB Esters ...................................................................... 13 1. Deprotection with Brønsted Acids ........................................................ 13 2. Deprotection with Lewis Acids ............................................................ 15 3. Deprotection Using Base-mediated Hydrolysis ....................................... 17 4. Deprotection by Hydrogenation ........................................................... 17 5. Deprotection by Oxidative Methods...................................................... 18 6. Deprotection by Photochemical Methods............................................... 20 III. Examples of the Use of PMB Esters ........................................................... 20 1. Examples of the Use of PMB Esters in Total Syntheses............................ 20 2. Examples in Methodology Development ............................................... 28 3. Other Examples ................................................................................. 30 Summary and Conclusion ......................................................................... 31 Acknowledgments .................................................................................... 31 References ............................................................................................... 32

中文翻译:

4-甲氧基苄酯的制备及其在有机合成中的应用

介绍 ................................................. ...................................................... 2 一. 形成PMB 酯 ..................................... ...................................... 3 1. 来自羧酸...................................... …………………………………………………………………………………………………………………………………………………………………………………… ...... 3 2. 来自活性酯...................................... ...................................... 8 3. 来自其他酯类和酰亚胺类...... …………………………………………………………………………………………………………………………………………………………………… ........ 9 4. 来自醛类 ..................................... ...................................................... 12 二.PMB 酯的脱保护 ..................................... ...................................... 13 1. 使用布朗斯台德酸脱保护 ..................... ...................................... 13 2. 路易斯酸脱保护 ...... .. …………………………………………………………………………………………………………………………………………………………………… .. 15 3. 使用碱介导的水解脱保护 ..................................................... 17 4. 加氢脱保护 ..................................... ..................................... 17 5. 氧化法脱保护 ..................................... ...................................... 18 6. 光化学方法脱保护 ..................................... ...................................... 20 三.PMB 酯的使用示例 ..................................................... ...................... 20 1. 在全合成中使用 PMB 酯的例子...................................... ...................... 20 2. 方法开发中的例子...................................................... ...................... 28 3. 其他示例 ...................................... ..................................................... 30 总结和结论 ............................
更新日期:2016-01-02
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