Addition of nitromethane to the chiral chromium tricarbonyl complex of o-tolualdehyde (1) gives, under conditions of kinetic control, the nitroalcohol 2 with ∼95% of asymmetric induction. Compound 2 then gives, in 3 steps, the corresponding aminoalcohol in about 40% yield. Use of nitroethane gives the nitroalcohol with a small diastereoselectivity at C(2)-C(3) (d.e. = 30 and 55%), but analogs of ephedrine and pseudoephedrine can be obtained optically pure by chromatography.

ASYMMETRIC-SYNTHESIS OF EPHEDRINE ANALOGS / A. SOLLADIE-CAVALLO, G. LAPITAJS, P. BUCHERT, A. KLEIN, S. COLONNA, A. MANFREDI. - In: JOURNAL OF ORGANOMETALLIC CHEMISTRY. - ISSN 0022-328X. - 330:3(1987 Aug), pp. 357-363.

ASYMMETRIC-SYNTHESIS OF EPHEDRINE ANALOGS

A. MANFREDI
Ultimo
1987

Abstract

Addition of nitromethane to the chiral chromium tricarbonyl complex of o-tolualdehyde (1) gives, under conditions of kinetic control, the nitroalcohol 2 with ∼95% of asymmetric induction. Compound 2 then gives, in 3 steps, the corresponding aminoalcohol in about 40% yield. Use of nitroethane gives the nitroalcohol with a small diastereoselectivity at C(2)-C(3) (d.e. = 30 and 55%), but analogs of ephedrine and pseudoephedrine can be obtained optically pure by chromatography.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/187936
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