TRICARBONYLCHROMIUM(0) PROMOTED STEREOSELECTIVE TRANSFORMATIONS OF EPHEDRINE AND PSEUDOEPHEDRINE DERIVATIVES

被引：24

作者：

COOTE, SJ ^{[1
]}

DAVIES, SG ^{[1
]}

GOODFELLOW, CL ^{[1
]}

SUTTON, KH ^{[1
]}

MIDDLEMISS, D ^{[1
]}

NAYLOR, A ^{[1
]}

机构：

[1] GLAXO GRP RES LTD,WARE SG12 0DJ,HERTS,ENGLAND

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 11期

关键词：

D O I：

10.1016/S0957-4166(00)80447-4

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

(-)-(1S,2S)-(N,O-Dimethylephedrine)tricarbonyl chromium(0) (6) and (-)-(1S,2R)-(N,O-dimethylpseudoephedrine)tricarbonylchiromium(0) (22) undergo completely stereoselective ortho deprotonation upon treatment with alkyllithium base, followed by addition of an electrophile. In both cases, exclusive removal of the pro-(R)-ortho proton was confirmed by single crystal X-ray structure analyses of the methylated products. Addition of methyllithium onto the ortho-formylated derivative of complex (6) occurs stereoselectively, the stereochemistry of the major product being confirmed by a single crystal X-ray structure determination. The results presented demonstrate an efficient transfer of chirality from a side chain onto the (arene)tricarbonylchromium(0) complex and back to a different side chain. © 1990.

引用

页码：817 / 842

页数：26

共 32 条

[1]

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