Nonsilyl Bicyclic Secondary Amine Catalysts for the Asymmetric Transfer Hydrogenation of α,β-Unsaturated Aldehydes

被引：0

作者：

Kumar, Rohtash ^{[1
]}

Maurya, Vidyasagar ^{[1
]}

Avinash, Avinash ^{[1
]}

Appayee, Chandrakumar ^{[1
]}

机构：

[1] Indian Inst Technol Gandhinagar, Dept Chem, Gandhinagar 382055, Gujarat, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 12期

关键词：

DIARYLPROLINOL SILYL ETHERS; CONJUGATE REDUCTION; MICHAEL ADDITION; DESIGN; ALKYLATION; EFFICIENT; ORGANOCATALYSTS; REAGENTS; ALCOHOLS;

D O I：

10.1021/acs.joc.4c00523

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first chiral synthesis of nonsilyl bicyclic secondary amine organocatalysts and their application to the asymmetric transfer hydrogenation of alpha,beta-unsaturated aldehydes are disclosed. A lower catalytic loading (5 mol %) is demonstrated for the reduction of a wide range of alpha,beta-unsaturated aldehydes (up to 97% yield and up to 99% ee). The application of this scalable methodology is showcased for the asymmetric synthesis of bioactive molecules such as phenoxanol, citronellol, ramelteon, and terikalant.

引用

页码：8586 / 8600

页数：15

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