Titanocene-Catalyzed Regiodivergent Epoxide Opening - From Desymmetrizingmeso-Epoxides to Regiodivergent Arylation of Epoxides

被引：11

作者：

Weissbarth, Hendrik ^{[1
]}

Muehlhaus, Felix ^{[1
]}

Gansaeuer, Andreas ^{[1
]}

机构：

[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, Gerhardt Domagk Str 1, D-53121 Bonn, Germany

来源：

SYNTHESIS-STUTTGART | 2020年 / 52卷 / 20期

关键词：

arylation; catalysis; diversity-oriented synthesis; epoxides; regiodivergent; titanocenes; ENANTIOSELECTIVE ADDITION; ORGANOMETALLIC REAGENTS; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; RADICALS; DESYMMETRIZATION; COMPLEXES; CHEMISTRY; LIGANDS; TOOL;

D O I：

10.1055/s-0040-1706403

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

While S(N)2 based desymmetrization of meso-epoxides has been extensively researched, the more general regioselective opening of cis-1,2 substituted epoxides via S(N)2 mechanism remains elusive. This short review outlines, how this limitation could be overcome by parting with S(N)2 and moving towards a radical-based mechanism. The development and refinement of the titanocene(III)-catalyzed regiodivergent epoxide opening (REO) is described.

引用

页码：2940 / 2947

页数：8

共 34 条

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[34] A RATIONAL APPROACH TO CHIRAL ALPHA-HYDROXY ARYL KETONES FROM CHIRAL ARYL EPOXIDES VIA REGIOSELECTIVE, STEREO RETENTIVE OXIDATIVE EPOXIDE OPENING - ITS APPLICATION TO THE SYNTHESIS OF ANTIFUNGAL SCH-42427 SM-9164
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