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

doi:10.6023/cjoc202309020

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1293-1300.DOI: 10.6023/cjoc202309020 Previous Articles Next Articles

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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^b, 杨福美^a, 陈明瀚^a, 孙德立^c^,^*(), 叶丹锋^a^,^*()

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 发布日期:2023-11-30
基金资助:
宁波工程学院(2130011540027)

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

Yunhui Wan^b, Fumei Yang^a, Minghan Chen^a, Deli Sun^c(), Danfeng Ye^a()

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

Received:2023-09-20 Revised:2023-11-18 Published:2023-11-30
Contact: * E-mail: 13023288301@163.com; sundeli220@163.com
Supported by:
Ningbo University of Technology(2130011540027)

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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

Cite this article

Yunhui Wan, Fumei Yang, Minghan Chen, Deli Sun, Danfeng Ye. Esterification of N-Benzyl-N-t-butoxycarbonyl-amides and Unsaturated Alcohol under Transition Metal-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2024, 44(4): 1293-1300.

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Fig. & Tab. 6

Scheme 1. Previous studies on esterification of amides

Entry	Base	Solvent	Yield^b/%
1	Cs₂CO₃	DMF	81
2	CsF	DMF	9
3	K₂CO₃	DMF	45
4	t-BuOLi	DMF	94
5	t-BuOK	DMF	79
6	KF	DMF	0
7	t-BuOLi	DMSO	91
8	t-BuOLi	CH₃OH	Trace
9	t-BuOLi	THF	53
10	t-BuOLi	DCM	69

Table 1. Optimization of reaction condition

Table 2. Substrate scope of amides

Table 3. Substrate scope of unsaturated alcohols

Scheme 2. Modification of natural products and drug molecules

Scheme 3. Probable mechanism for the esterification of N- benzyl-N-t-butoxycarbonyl-amides

References 33

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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

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

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Fig. & Tab. 6

References 33

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