Asymmetric Phase-Transfer Alkylation of Readily Available Aryl Aldehyde Schiff Bases of Amino Acid Ethyl Esters

被引：6
|
作者：
Lu, Jinying [1 ,2 ]
Huang, Lei [1 ,2 ]
Liang, Huatai [1 ,2 ]
Wang, Zhe [1 ,2 ]
Kato, Terumasa [1 ,2 ,3 ]
Liu, Yan [1 ,2 ]
Maruoka, Keiji [1 ,2 ,3 ]
机构：
[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China
[2] Guangdong Univ Technol, Guangdong Prov Key Lab Plant Resources Biorefinery, Guangzhou 510006, Peoples R China
[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Lab Organocatalyt Chem, Sakyo Ku, Kyoto 6068501, Japan
来源：
ORGANIC LETTERS | 2024年 / 26卷 / 20期
基金：
中国国家自然科学基金;
关键词：
CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ALPHA-AMINO; ALPHA; ALPHA-DIALKYL-ALPHA-AMINO ACIDS; AMMONIUM-SALTS; DERIVATIVES; DISCOVERY; PEPTIDES; DESIGN; MILD;
D O I：
10.1021/acs.orglett.3c04290
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric phase-transfer alkylation of the N-(arylmethylene)-alpha-alkylamino acid ethyl esters and N-(arylmethylene)glycine ethyl esters was found to be catalyzed by the (R)- or (S)-Simplified Maruoka Catalyst with high efficiency and excellent enantioselectivity. This approach was successfully applied to the enantioselective formal synthesis of the angiotensin II type 2 receptor (AT2R) antagonists Olodanrigan and LX9211, and the practical aspect is demonstrated by the kilogram-scale synthesis of a key intermediate for the synthesis of LX9211.
引用
收藏
页码：4163 / 4167
页数：5
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