THE HIGHLY STEREOSELECTIVE CONVERSION OF N,N-DIMETHYLAMPHETAMINE INTO N-METHYLPSEUDOEPHEDRINE - A MIMIC OF THE ENZYME MEDIATED STEREOSPECIFIC BENZYLIC HYDROXYLATION OF 2-ARYLETHYLAMINES

被引：17

作者：

BLAGG, J ^{[1
]}

DAVIES, SG ^{[1
]}

机构：

[1] DYSON PERRINS LAB, S PARKS RD, OXFORD OX1 3QY, ENGLAND

来源：

TETRAHEDRON | 1987年 / 43卷 / 19期

关键词：

D O I：

10.1016/S0040-4020(01)90323-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of (S)-(n6-N,N-dimethylamphetamine)Cr(CO)3 with n-butyllithium below -40.degree.C gives a stable benzylic carbanion via loss of the pro-R-benzylic proton. Warming of this anion above -40.degree.C gives (n6-E-.beta.-methylstyrene)Cr(CO)3 via an ElcB type elimination whilst trapping with an electrophile below -40.degree.C gives benzylically functionalised amphetamines with overall retention of configuration. The use of oxodiperoxymolybdenum(pyridine)hexamethylphosphoramide as the electrophile gives optically pure (1S,2S)-N-methylpseudoephedrine after decomplexation.

引用

页码：4463 / 4471

页数：9

共 30 条

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