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.
Titolo: | ASYMMETRIC-SYNTHESIS OF EPHEDRINE ANALOGS |
Autori: | MANFREDI, AMEDEA GIUSEPPINA (Ultimo) |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | ago-1987 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/S0022-328X(00)99049-1 |
Appare nelle tipologie: | 01 - Articolo su periodico |