Photoinduced, Palladium-Catalyzed Enantioselective 1,2-Alkylsulfonylation of 1,3-Dienes

被引：4

作者：

Liu, Zhi-Lin ^{[1
]}

Ye, Zhi-Peng ^{[1
]}

Liao, Zi-hao ^{[1
]}

Lu, Wei-Dong ^{[1
]}

Guan, Jian-Ping ^{[1
]}

Gao, Zi-Yi ^{[1
]}

Chen, Kai ^{[1
]}

Chen, Xiao-Qing ^{[1
]}

Xiang, Hao-Yue ^{[1
,2
]}

Yang, Hua ^{[1
]}

机构：

[1] Cent South Univ, Coll Chem & Chem Engn, Changsha 410083, Peoples R China

[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China

来源：

ACS CATALYSIS | 2024年 / 14卷 / 05期

基金：

中国国家自然科学基金;

关键词：

chiral allylic sulfonylated compounds; 1,3-dienes; excited-state palladium catalysis; asymmetric alkylsulfonylation; photochemical; allylic substitution; CYCLIC SULFONES; ALKYL-HALIDES; HECK REACTION; PHOTOREDOX; NICKEL; BONDS;

D O I：

10.1021/acscatal.4c00470

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：

The chiral allylic sulfonylated group is a unique structural motif embedded in a range of natural products and pharmaceuticals. Notably, the synthesis of structurally diverse chiral allylic sulfonylated derivatives via alkylsulfonylation of 1,3-dienes remains underexplored because of its inherent challenges in stereocontrol and regioselectivity. Herein, photoinduced, palladium-catalyzed enantioselective 1,2-alkylsulfonylation of conjugated 1,3-dienes is described. A wide variety of alkyl bromides, 1,3-dienes, and sodium sulfinates could be facilely coupled to generate value-added chiral allylic sulfonylated derivatives with high enantioselectivity. Finally, the utility of this enantioselective difunctionalization protocol was demonstrated in pharmaceutical analogue synthesis.

引用

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页码：3725 / 3732

页数：8

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