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Treatment of (S)-(η6-N,N-dimethylamphetamine)Cr(CO)3, with n-butyllithium below -40°C gives a stable benzylic carbanion via loss of the pro-R-benzylic proton. Warming of this anion above -40°C gives (η6-E-β-methylstyrene)Cr(CO)3 via an ElcB type elimination whilst trapping with an electrophile below -40°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. © 1987.

Original publication

DOI

10.1016/S0040-4020(01)90323-0

Type

Journal article

Journal

Tetrahedron

Publication Date

01/01/1987

Volume

43

Pages

4463 - 4471