Lewis Acid-Catalyzed Carbofunctionalization of Uncommon C,N-Diacyliminium Ions: Controlling Regio- and Enantioselectivity

被引：14

作者：

Gronbach, Lisa Marie ^{[1
]}

Voss, Alice ^{[1
]}

Frahm, Mario ^{[1
]}

Villinger, Alexander ^{[1
]}

Bresien, Jonas ^{[1
]}

Michalik, Dirk ^{[1
,2
]}

Brasholz, Malte ^{[1
,2
]}

机构：

[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany

[2] Leibniz Inst Katalyse eV, D-18059 Rostock, Germany

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 20期

关键词：

INTERMOLECULAR ADDITION-REACTIONS; ACYLIMINIUM;

D O I：

10.1021/acs.orglett.1c02857

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The tricyclic azepino[1,2-a]indole acetates 7, readily accessible by visible-light-driven catalytic photooxygenation of cyclohepta[b]indoles 1, are convenient precursors to novel and uncommon cyclic C,N-diacyliminium ions 3. We report here the first Lewis acid-catalyzed C-C bond forming reactions of these species with TMSCN and silyl enol ethers as nucleophiles and utilizing TIPSOTf as well as Sc(OTf)(3) as catalysts. Employing Sc(OTf)(3)/pybox complexes as a chiral catalyst system, regio- and enantioselective asymmetric alkylations with silyl enol ethers were achieved.

引用

页码：7834 / 7838

页数：5

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