手性辅基诱导β-脱氢氨基酸酯的非均相不对称氢化(英文)

doi:10.6023/cjoc201701020

有机化学 ›› 2017, Vol. 37 ›› Issue (6): 1398-1406.DOI: 10.6023/cjoc201701020 上一篇下一篇

研究论文

手性辅基诱导β-脱氢氨基酸酯的非均相不对称氢化(英文)

王群^a, 江黎黎^a, 卢斌^a, 胡北^a, 谢小敏^a,b, 李泽标^b, 张兆国^a

a. 上海交通大学化学化工学院上海 200240;
b. 南通常佑制药有限公司南通 226400

收稿日期:2017-01-09 修回日期:2017-02-28 发布日期:2017-03-03
通讯作者: 张兆国 E-mail:zhaoguo@sjtu.edu.cn
基金资助:
国家自然科学基金（No.21472124）资助项目.

Pt/Al₂O₃ Catalyzed Diastereoselective Hydrogenation of β-Dehydro-amino Esters Induced by a Chiral Prosthetic Group

Wang Qun^a, Jiang Lili^a, Lu Bin^a, Hu Bei^a, Xie Xiaomin^a,b, Li Zebiao^b, Zhang Zhaoguo^a

a. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240;
b. Nantong Changyou Pharmaceutical Company, Nantong 226400

Received:2017-01-09 Revised:2017-02-28 Published:2017-03-03
Contact: 10.6023/cjoc201701020 E-mail:zhaoguo@sjtu.edu.cn
Supported by:
Project supported by the National Natural Sciences Foundation of China (No. 21472124).

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1. 手性辅基诱导β-脱氢氨基酸酯的非均相不对称氢化(英文).PDF(1489KB)

摘要/Abstract

研究了手性辅基诱导Pt/Al₂O₃催化的β-脱氢氨基酸酯的非均相不对称氢化，成功地氢化了一系列β-脱氢氨基酸酯的底物，得到了很好的转化率和dr值（dr值可高达5.2：94.8）.提供了一种非常高效、便捷的关于β-脱氢氨基酸酯的不对称氢化方法，产物可以作为西他列汀药物重要中间体.

关键词: 西他列汀, 非对映选择性, β-脱氢氨基酸酯, Pt/Al₂O₃, 非均相不对称氢化

A chiral prosthetic group induced heterogeneous diastereoselective asymmetric hydrogenation of β-dehydroamino esters, catalyzed by Pt/Al₂O₃, has been developed. A series of β-dehydroamino esters were successfully hydrogenated in high yields with good diastereoselectivities (dr up to 5.2:94.8). This method provides a convenient and efficient synthetic way for the preparation of chiral β-amino acid derivatives, which are key intermediates for bioactive compounds and pharmaceuticals.

Key words: sitagliptin, diastereoselectivities, β-dehydroamino esters, Pt/Al₂O₃, heterogeneous hydrogenation

引用此文

王群, 江黎黎, 卢斌, 胡北, 谢小敏, 李泽标, 张兆国. 手性辅基诱导β-脱氢氨基酸酯的非均相不对称氢化(英文)[J]. 有机化学, 2017, 37(6): 1398-1406.

Wang Qun, Jiang Lili, Lu Bin, Hu Bei, Xie Xiaomin, Li Zebiao, Zhang Zhaoguo. Pt/Al₂O₃ Catalyzed Diastereoselective Hydrogenation of β-Dehydro-amino Esters Induced by a Chiral Prosthetic Group[J]. Chin. J. Org. Chem., 2017, 37(6): 1398-1406.

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手性辅基诱导β-脱氢氨基酸酯的非均相不对称氢化(英文)

Pt/Al₂O₃ Catalyzed Diastereoselective Hydrogenation of β-Dehydro-amino Esters Induced by a Chiral Prosthetic Group

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手性辅基诱导β-脱氢氨基酸酯的非均相不对称氢化(英文)

Pt/Al2O3 Catalyzed Diastereoselective Hydrogenation of β-Dehydro-amino Esters Induced by a Chiral Prosthetic Group

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Pt/Al₂O₃ Catalyzed Diastereoselective Hydrogenation of β-Dehydro-amino Esters Induced by a Chiral Prosthetic Group