Functionalization of Acetalic C(sp3)-H Bonds by Scandium(III) Triflate-Catalyzed Intramolecular Redox Reactions: Tandem 1,4-Hydride Transfer/1,5-Cyclization Processes Leading to Protected 1-Indanones

被引：51

作者：

Alajarin, Mateo ^{[1
]}

Marin-Luna, Marta ^{[1
]}

Vidal, Angel ^{[1
]}

机构：

[1] Univ Murcia, Fac Quim, Dept Quim Organ, E-30100 Murcia, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 04期

关键词：

acetals; cyclization; 1,4]-H shift; intramolecular hydride transfer; scandium triflate; C-H FUNCTIONALIZATION; ALKYNYL ETHERS; CYCLIZATION; HYDROALKYLATION; ALKYLATION; COMPLEXES; PLATINUM;

D O I：

10.1002/adsc.201000812

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A new C-C bond forming reaction leading to adjacent quaternary carbons is reported. It is a one-pot hydride shift/cyclization process facilitated by the hydricity of the acetalic C H bonds, with benzylidenemalonate fragments as electrophilic hydride acceptors, and the catalysis of scandium(III) triflate. The reaction products are 1,2-dihydroindane derivatives. Alkoxy and alkanethiolate groups can be also intramolecularly transferred from the acetalic carbon to the electrophilic benzylidenemalonate C=C bond.

引用

页码：557 / 562

页数：6

共 42 条

[1] Tandem 1,5-Hydride Shift/1,5-S,N-Cyclization with Ethylene Extrusion of 1,3-Oxathiolane-Substituted Ketenimines and Carbodiimides. An Experimental and Computational Study [J].