Synthesis of cyclopropanes through gold-catalyzed [2+1] cycloaddition of allenamides with sulfoxonium ylides

被引：2

作者：

Hong, Tong ^{[1
]}

Liu, Yongchun ^{[1
]}

Zhao, Kun ^{[1
]}

Cheng, Song ^{[1
]}

Liu, Qingsong ^{[1
]}

Zhang, Shuting ^{[1
]}

Zhong, Ying ^{[1
]}

Li, Xiaoxiao ^{[1
]}

Zhao, Zhigang ^{[1
]}

机构：

[1] Southwest Minzu Univ, Sch Chem & Environm, Key Lab Basic Chem State Ethn Commiss, Chengdu 610041, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 17期

关键词：

N-ALLENYL AMIDES; ENANTIOSELECTIVE CYCLOPROPANATION; PRECURSOR; IMINIUM; MILD;

D O I：

10.1039/d3ob00390f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclopropyl groups are widely found in pharmaceutical products and their application as precursors or key reaction intermediates benefits the development of a wide range of reactions. Herein, we report a facile protocol for the synthesis of this compound through gold-catalyzed [2 + 1] cycloaddition of allenamides with sulfoxonium ylides. The reaction exhibited good functional group tolerance and high efficiency, affording the products in good to excellent yields with good diastereoisomerism. The steric hindrance between the sulfonamide group and the gold catalyst determined the major configuration of the formed cis-cyclopropane product. Moreover, the aldehyde could be converted to amide under Schmidt reaction conditions and alcohol under reduction conditions.

引用

页码：3684 / 3690

页数：7

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