Photochemical organocatalytic enantioselective radical γ-functionalization of α-branched enals

被引：11

作者：

Balletti, Matteo ^{[1
,2
]}

Marcantonio, Enrico ^{[1
]}

Melchiorre, Paolo ^{[1
,3
]}

机构：

[1] Barcelona Inst Sci & Technol, ICIQ Inst Chem Res Catalonia, Av Paisos Catalans 16, Tarragona 43007, Spain

[2] Univ Rovira & Virgili URV, Dept Analyt Chem & Organ Chem, Tarragona 43007, Spain

[3] ICREA Catalan Inst Res & Adv Studies, Spain Pmelchiorre Iciqes, Pg Lluis Co 23, Barcelona 08010, Spain

来源：

CHEMICAL COMMUNICATIONS | 2022年 / 58卷 / 41期

关键词：

ALPHA; BETA-UNSATURATED ALDEHYDES; REMOTE FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; ALKYLATION; CATALYSIS; CYCLOADDITION; DERIVATIVES; PRINCIPLE; VINYLOGY;

D O I：

10.1039/d2cc01638a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Reported herein is a rare example of asymmetric catalytic functionalisation of enals at the remote gamma-position, proceeding via a radical path. The process requires visible light and exploits the synergistic actions of two distinct organocatalysts. A nucleophilic organic catalyst generates radicals upon S(N)2-based activation of commercially available alkyl halides and blue light irradiation. Concomitantly, a chiral secondary amine catalyst triggers the formation of a dienamine from alpha-branched enals. This chiral dienamine intercepts the photogenerated radicals with excellent gamma-selectivity and good stereocontrol.

引用

页码：6072 / 6075

页数：4

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