Direct conjugate alkylation of α,β-unsaturated carbonyls by TiIII-catalysed reductive umpolung of simple activated alkenes

被引：27

作者：

Bichovski, Plamen ^{[1
]}

Haas, Thomas M. ^{[1
]}

Keller, Manfred ^{[1
]}

Streuff, Jan ^{[1
]}

机构：

[1] Univ Freiburg, Inst Organ Chem, Albertsrasse 21, D-79104 Freiburg, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 24期

关键词：

ARYL IODIDES; ENANTIOSELECTIVE CONSTRUCTION; QUATERNARY CENTERS; ARYLBORONIC ACIDS; ORGANIC HALIDES; BOND FORMATION; ENONES; ADDITIONS; 1,4-ADDITION; DIMERIZATION;

D O I：

10.1039/c5ob02631h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The titanium(III)-catalysed cross-selective reductive umpolung of Michael-acceptors represents a unique direct conjugate beta-alkylation reaction. It allows the cross-selective preparation of 1,6- and 1,4-difunctionalised building blocks without the requirement of stoichiometric organometallic reagents. In this full paper, the development and scope of the titanium(III)-catalysed cross-selective reductive umpolung of Michael-acceptors is described. Based on the observed selectivities and additional mechanistic experiments a refined mechanistic proposal is presented.

引用

页码：5673 / 5682

页数：10

共 77 条

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