β-氨基羰基化合物合成研究及其应用:(+)-Sedridine的全合成

doi:10.6023/cjoc201710022

有机化学 ›› 2018, Vol. 38 ›› Issue (1): 131-137.DOI: 10.6023/cjoc201710022 上一篇下一篇

所属专题：庆祝吴养洁院士九十华诞专辑

研究论文

β-氨基羰基化合物合成研究及其应用:(+)-Sedridine的全合成

孙凯^a, 孙兴文^a, 林国强^a,b

a 复旦大学化学系上海 200433;
b 中国科学院上海有机化学研究所上海 200032

收稿日期:2017-10-20 修回日期:2017-10-31 发布日期:2017-11-03
通讯作者: 孙兴文 E-mail:sunxingwen@fudan.edu.cn
基金资助:
国家自然科学基金（No.20802009）资助项目.

Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine

Sun Kai^a, Sun Xingwen^a, Lin Guoqiang^a,b

a Department of Chemistry, Fudan University, Shanghai 200433;
b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2017-10-20 Revised:2017-10-31 Published:2017-11-03
Contact: 10.6023/cjoc201710022 E-mail:sunxingwen@fudan.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 20802009).

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摘要/Abstract

β-氨基羰基结构广泛存在于具有生理活性的小分子及药物中，并且是重要的合成砌块，可方便地转化为其它结构和片段.报道了一种新的制备β-氨基羰基化合物的方法.该方法使用氧气为氧化剂，醋酸钯、氯化亚铜为催化剂，可将手性高烯丙基胺类化合物转化为相应的β-氨基羰基化合物.该方法产率良好，底物适应性好，不影响分子中已有的手性中心.利用该方法完成了天然产物分子（+）-Sedridine的全合成工作，总收率32%.

关键词: β-氨基羰基化合物, 手性高烯丙基胺, Wacker反应, (+)-Sedridine

β-Amino-carbonyl fragments are important structures of many bioactive molecules and pharmaceuticals and critical synthetic blocks which can be easily converted into other structures and compounds. A novel method for preparing β-amino-carbonyl compounds with oxygen as an oxidant, palladium acetate and cuprous chloride as catalysts was reported. The chiral high allyl amine compounds can be converted into corresponding β-amino carbonyl compounds with moderate to good yield, good substrate scope, and tolerance of chiral centers. Natural product (+)-sedridine was synthesized with 32% yield.

Key words: β-amino carbonyl compound, chiral high allyl amine, Wacker reaction, (+)-sedridine

引用此文

孙凯, 孙兴文, 林国强. β-氨基羰基化合物合成研究及其应用:(+)-Sedridine的全合成[J]. 有机化学, 2018, 38(1): 131-137.

Sun Kai, Sun Xingwen, Lin Guoqiang. Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine[J]. Chin. J. Org. Chem., 2018, 38(1): 131-137.

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β-氨基羰基化合物合成研究及其应用:(+)-Sedridine的全合成

Synthesis of β-Amino Carbonyl Compounds and Its Application: Total Synthesis of (+)-Sedridine

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