Chiral base mediated asymmetric synthesis of tricarbonyl(eta(6)-arene)-chromium complexes

被引:77
作者
Ewin, RA
MacLeod, AM
Price, DA
Simpkins, NS
Watt, AP
机构
[1] UNIV NOTTINGHAM,DEPT CHEM,NOTTINGHAM NG7 2RD,ENGLAND
[2] MERCK SHARP & DOHME RES LABS,HARLOW CM20 2QR,ESSEX,ENGLAND
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 04期
关键词
D O I
10.1039/a605812d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enantiomerically enriched tricarbonyl(eta(6)-arene)chromium complexes can be obtained in up to 94% ee from the enantioselective ortho-metallation reaction of certain symmetrically substituted complexes with Me(3)SiCl, mediated by a chiral lithium amide base. The level of asymmetric induction depends upon the nature of the starting ring substituent(s) and, in the case of anisole-type complexes, a proton transfer reaction involving the chiral metallated intermediate and the neutral tricarbonyl(eta(6)-arene)chromium complex results in rapid racemisation in the absence of an in situ electrophilic quench. Non-racemic derivatives of a tricarbonyl(eta(6)-arene)chromium complex derived from 1,3-dihydroisobenzofuran are also prepared in up to 99% ee by chiral base deprotonation, and trends in the regioselectivity of metallation of this complex with a range of lithium amide bases are described.
引用
收藏
页码:401 / 415
页数:15
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