Asymmetric synthesis of axially chiral biaryls: Inversion of planar chirality vs axial isomerization and functionalization at the side chain of biaryl chromium complexes

被引：29

作者：

Kamikawa, K

Sakamoto, T

Tanaka, Y

Uemura, M ^{[1
]}

机构：

[1] Osaka Prefecture Univ, Fac Integrated Arts & Sci, Dept Chem, Sakai, Osaka 5998531, Japan

[2] Osaka Prefecture Univ, Res Inst Adv Sci & Technol, Sakai, Osaka 5998570, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 24期

关键词：

D O I：

10.1021/jo0302307

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Axially chiral syn-biaryl chromium complexes having a coordinating heteroatom substituent at the benzylic position gave anti-biaryl chromium complexes 5 with inversion of the planar chirality by heating in a nonaromatic solvent, while syn-biaryl chromium complexes with an o-methyl or formyl substituent afforded axially isomerized anti-biaryl chromium complexes under heating in an aromatic solvent. syn-Biaryl and both enantiomeric anti-biaryl chromium complexes with the o-formyl group were stereoselectively prepared from an identical planar chiral arene chromium complex as chiral source. The formyl group of the axially chiral chromium complexes was functionalized by radical cyclization and beta-lactam formation, and hetero-Diels -Alder reaction.

引用

页码：9356 / 9363

页数：8

共 67 条

[1] ENANTIOSELECTIVE ORTHO-LITHIATION OF BENZALDEHYDE CHROMIUMTRICARBONYL COMPLEX [J].