Rhodium-Catalyzed Hydrocarbonylation of a Homoallylamine via N-H Activation and Application for Synthesis of Yohimbane Alkaloids

被引：11

作者：

Chiou, Wen-Hua ^{[1
]}

Wang, Yu-Wei ^{[1
]}

Kao, Chien-Lun ^{[1
]}

Chen, Po-Chou ^{[1
]}

Wu, Chen-Chang ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 40227, Taiwan

来源：

ORGANOMETALLICS | 2014年 / 33卷 / 16期

关键词：

ALLOYOHIMBANE ALKALOIDS; INDOLE ALKALOIDS; CYCLIZATION; SYSTEMS; AMINES; (+/-)-ALLOYOHIMBANE; (-)-ALLOYOHIMBANE; HYDROFORMYLATION; CARBONYLATION; (-)-YOHIMBANE;

D O I：

10.1021/om500498u

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We describe syntheses of n-yohimbane and alloyohimbane using Rh-catalyzed hydrocarbonylation, which provides a practical methodology to synthesize a delta-lactam from a secondary homoallyl amine. We have also observed an unexpected transformation where the amine proton served as a hydride to participate in hydrocarbonylation. The D-labeled experimental results and preliminary DFT-calculations suggest that the transformation can be rationalized by oxidative cleavage of the homoallyl amines to a metal hydride complex.

引用

页码：4240 / 4244

页数：5

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