Citation: Zhang Pengpeng, Han Shenghua, Chen Jianxin. Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source[J]. Chinese Journal of Organic Chemistry, ;2020, 40(6): 1737-1744. doi: 10.6023/cjoc202001020 shu

Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source

a.
College of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041004
b.
College of Chemistry and Engineering, Shanxi Datong University, Datong, Shanxi 037009

Corresponding author: Chen Jianxin, jjxxcc2002@yahoo.com
Received Date: 14 November 2019
Revised Date: 4 March 2020
Available Online: 31 March 2020
Fund Project: the Natural Science Foundation of Shanxi Province 2012011046-9the Shanxi Provincal Foundation for Returnees Overseas Scientists 0713Project supported by the Shanxi Provincal Foundation for Returnees Overseas Scientists (No. 0713), and the Natural Science Foundation of Shanxi Province (No. 2012011046-9)

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The selective aminocarbonylation of vicinal diketones using carbamoylsilane as an amide source affords β-keto-α-siloxyamide derivatives in 62%~90% yields under mild conditions without using any oxidants and catalysts. The steric hindrance, which is both from the groups of vicinal diketones and the carbamoylsilanes, affects reaction selectivity on two carbonyl groups. The methoxymethyl or benzyl used as an amino protecting group, can be easily converted into hydrogen atom leading to β-keto-α-hydroxy secondary or primary amides. The simple procedure allows the preparation of various β-keto-α-hydroxy amide derivatives including primary, secondary and tertiary β-keto-α-hydroxy amide derivatives. The reaction has the advantages of mild conditions, less by-products, high selectivity, good yield and simple post-treatment, and it is a new method for the efficient preparation of β-keto-α-hydroxyamides.
- carbamoylsilanes,
- β-keto-α-hydroxyamides,
- aminocarbonylation,
- nucleophilic addition,
- vicinal diketones
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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Efficient Synthesis of β-Keto-α-hydroxy Secondary (Primary) Amides by Selective Aminocarbonylation of Vicinal Diketones Using Carbamoylsilane as an Amide Source

南开大学师唯/华北电力大学（保定）刘景维：二维配位聚合物中有序的亲锂冠醚位点用于无枝晶锂沉积

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通讯作者: 陈斌, bchen63@163.com