Gold-Catalyzed Domino Cycloisomerization/Alkoxylation: An Entry to 3,4-Dihydro-1H-[1,4]oxazino[4,3-a]indole

被引：9

作者：

Dupeux, Aurelien ^{[1
]}

Michelet, Veronique ^{[1
]}

机构：

[1] Cote dAzur Univ, Inst Chim Nice, F-06108 Nice 2, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 86卷 / 24期

关键词：

CYCLIC ALKENYL ETHERS; ENANTIOSELECTIVE FUNCTIONALIZATION; ORTHO-ALKYNYLBENZALDEHYDES; CYCLIZATION; SILVER; ADDITION/ANNULATION; COMPLEXES; PLATINUM; INDOLES; KETONES;

D O I：

10.1021/acs.joc.1c02030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and mild synthetic route for the preparation of functionalized polycyclic indole skeletons via a gold-mediated cycloisomerization/alkoxylation of 1,6-aldehyde-yne has been developed. This atom-economical catalytic process that associates IPrAu(MeCN)BF4 and an alcohol demonstrated remarkable selectivity in accessing functionalized 3,4-dihydro-1H-[1,4]oxazino[4,3-a]indole derivatives of high synthetic utility (21 examples, yields of <= 96%) and could be optimized under asymmetric conditions with an enantiomeric excess of <= 86%.

引用

页码：17738 / 17747

页数：10

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