Enantioselective Dehydrative γ-Arylation of α-Indolyl Propargylic Alcohols with Phenols: Access to Chiral Tetrasubstituted Allenes and Naphthopyrans

被引：48

作者：

Zhu, Wen-Run ^{[1
]}

Su, Qiong ^{[1
]}

Diao, Hong-Juan ^{[1
]}

Wang, Er-Xuan ^{[1
]}

Wu, Feng ^{[1
]}

Zhao, Yun-Long ^{[1
]}

Weng, Jiang ^{[1
]}

Lu, Gui ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab Chiral Mol & Drug Discover, Guangzhou 510006, Peoples R China

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 17期

基金：

中国国家自然科学基金;

关键词：

CATALYTIC ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; BRONSTED ACID; FUNCTIONALIZATION; PHOSPHATES; ALLENOATES;

D O I：

10.1021/acs.orglett.0c02386

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we report an enantioselective dehydrative gamma-arylation of alpha-indolyl propargylic alcohols with phenols via organocatalysis, which provides efficient access to chiral tetrasubstituted allenes and naphthopyrans in high yields with excellent regio- and enantioselectivities under mild conditions. This method features the use of cheaply available naphthols/phenols as the C-H aryl source and liberating water as the sole byproduct. Control experiments suggest that the excellent enantioselectivity and remote regioselectivity stem from dual hydrogen-bonding interaction with the chiral phosphoric acid catalyst.

引用

收藏

页码：6873 / 6878

页数：6

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