Synthesis of bridged tricyclo[5.2.1.0(1,5)]decanes via nickel-catalyzed asymmetric domino cyclization of enynones

作者:Chen, JC (Chen, Jiachang)[ 1 ] ; Wang, YM (Wang, Yiming)[ 1 ] ; Ding, ZT (Ding, Zhengtian)[ 1 ] ; Kong, WQ (Kong, Wangqing)[ 1 ]

NATURE COMMUNICATIONS

卷: 11 期: 1

文献号: 1882

DOI: 10.1038/s41467-020-15837-1

出版年: APR 20 2020

文献类型:Article

摘要

The restricted availability, expense and toxicity of precious metal catalysts such as rhodium and palladium challenge the sustainability of synthetic chemistry. As such, nickel catalysts have garnered increasing attention as replacements for enyne cyclization reactions. On the other hand, bridged tricyclo[5.2.1.0(1,5)]decanes are found as core structures in many biologically active natural products; however, the synthesis of such frameworks with high functionalities from readily available precursors remains a significant challenge. Herein, we report a nickel-catalyzed asymmetric domino cyclization reaction of enynones, providing rapid and modular synthesis of bridged tricyclo[5.2.1.0(1,5)]decane skeletons with three quaternary stereocenters in good yields and remarkable high levels of regio- and enantioselectivities (92-99% ee). Tricyclo[5.2.1.0(1,5)]decanes are often found in bioactive natural products; however, their synthesis poses significant challenges. Here, the authors report a nickel-catalyzed asymmetric domino cyclization of enynones, providing a rapid and modular synthesis of bridged tricyclo[5.2.1.0(1,5)]decane skeletons.

关键词

KeyWords Plus:STEREOCONTROLLED TOTAL-SYNTHESIS; ARYLATIVE CYCLIZATION; REDUCTIVE CYCLIZATION; BORYLATIVE CYCLIZATION; ALLYLIC ALCOHOLS; RHODIUM; ALKYNES; CYCLOISOMERIZATION; CARBOPALLADATION; CONSTRUCTION

作者信息

通讯作者地址:

Wuhan University Wuhan Univ, Ctr Precis Synth CPS, Inst Adv Studies IAS, Wuhan 430072, Peoples R China.

通讯作者地址: Kong, WQ (通讯作者)

Wuhan Univ, Ctr Precis Synth CPS, Inst Adv Studies IAS, Wuhan 430072, Peoples R China.

地址:

[ 1 ]‎ Wuhan Univ, Ctr Precis Synth CPS, Inst Adv Studies IAS, Wuhan 430072, Peoples R China

电子邮件地址:wqkong@whu.edu.cn