Organocatalytic Asymmetric Synthesis of Sulfonyl-Substituted Furans via a Cascade 1,6-Addition/Cyclization/Enantioselective Protonation Pathway

被引：0

作者：

Lian, Peng-Fei ^{[1
]}

Li, Zi-Hao ^{[1
]}

Qiu, Xin-Yue ^{[1
]}

Ding, Tong-Mei ^{[1
]}

Zhang, Shu-Yu ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Shanghai Key Lab Mol Engn Chiral Drugs, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

来源：

ACS CATALYSIS | 2024年 / 14卷 / 17期

关键词：

enantioselective protonation; asymmetric sulfonation; chiral sulfones; multisubstituted furans; organocatalyst; ENANTIOSELECTIVE PROTONATION; ADDITION-PROTONATION; INSERTION; ISOMERIZATION; CATALYSIS; STEREOCENTERS; ACTIVATION; CARBENES; ALCOHOLS; ALKYNES;

D O I：

10.1021/acscatal.4c03027

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

An efficient cascade 1,6-addition/cyclization/enantioselective protonation pathway between ene-yne-ketones and sodium sulfinates was realized. This protocol provides practical access to various sulfonyl-substituted furans in good yields and high enantioselectivities under mild reaction conditions. Control experiments and density functional theory calculations were conducted to elucidate the plausible reaction mechanism and the origins of stereoselectivity.

引用

页码：12717 / 12724

页数：8

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