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2024 , Vol. 44 >Issue 4: 1293 - 1300

DOI: https://doi.org/10.6023/cjoc202309020

研究论文

无过渡金属催化的N-苄基-N-叔丁氧羰基酰胺与不饱和醇的酯化反应

  • 万云辉 ,
  • 杨福美 ,
  • 陈明瀚 ,
  • 孙德立 ,
  • 叶丹锋
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  • a 宁波工程学院材料与化学工程学院 浙江宁波 315211
    b 上海大学理学院化学系 超分子化学与催化研究中心 上海 200444
    c 上海第二工业大学资源与环境工程学院 上海 201209

收稿日期: 2023-09-20

  修回日期: 2023-11-18

  网络出版日期: 2023-12-01

基金资助

宁波工程学院(2130011540027)

收起

Esterification of N-Benzyl-N-t-butoxycarbonyl-amides and Unsaturated Alcohol under Transition Metal-Free Conditions

  • Yunhui Wan ,
  • Fumei Yang ,
  • Minghan Chen ,
  • Deli Sun ,
  • Danfeng Ye
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  • a College of Material Science and Chemical Engineering, Ningbo University of Technology, Ningbo, Zhejiang 315211
    b Center for Supramolecular Chemistry & Catalysis, Department of Chemistry, College of Sciences, Shanghai University, Shanghai 200444
    c School of Resource and Environmental Engineering, Shanghai Polytechnic University, Shanghai 201209
* E-mail: ;

Received date: 2023-09-20

  Revised date: 2023-11-18

  Online published: 2023-12-01

Supported by

Ningbo University of Technology(2130011540027)

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摘要

报道了一种无过渡金属催化条件下N-苄基-N-叔丁氧羰基酰胺与不饱和醇的酯化反应. 在催化量叔丁醇锂的作用下, 高活性的N-叔丁氧羰基酰胺作为亲电试剂与不饱和醇发生酯化反应, 以优良的产率得到一系列不饱和酯类产物. 此外, 该反应体系无需昂贵的过渡金属催化, 具有反应条件相对温和等优点, 可进一步应用于天然产物和药物分子的后期修饰.

关键词： 无过渡金属催化; N-苄基-N-叔丁氧羰基酰胺; 不饱和醇; 酯化

本文引用格式

万云辉 , 杨福美 , 陈明瀚 , 孙德立 , 叶丹锋 . 无过渡金属催化的N-苄基-N-叔丁氧羰基酰胺与不饱和醇的酯化反应[J]. 有机化学, 2024 , 44(4) : 1293 -1300 . DOI: 10.6023/cjoc202309020

Abstract

A metal-free catalytic system for the esterification reaction of N-benzyl-N-t-butoxycarbonyl-amides with unsaturated alcohols was reported. With the assistance of catalytic amounts of lithium tert-butoxide, the highly reactive N-t-butoxy- carbonyl-amides were able to act as electrophiles and undergo esterification reactions with unsaturated alcohols to produce a series of unsaturated esters in excellent yields. Furthermore, this metal-free reaction system allowed relatively mild reaction conditions, making it a suitable choice for late-stage modification of natural products and drug molecules.

Key words： transition-metal-free catalysis; N-benzyl-N-t-butoxycarbonyl-amides; unsaturated alcohol; esterification

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