Stereoselective aldol reactions using ticl4 as stereochemical template

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Abstract

TiCl4 mediated aldol condensations establish multiple contiguous chiral centers in an almost complete enantio- and diastereoselective way.

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    Furthermore, derivatives of 2-amino-1-phenylpropane (e.g., 3–5; amphetamines) belong to the psychopharmacological active class of sympathomimetic drugs and are of pharmacological interest because they are used as stimulants, decongestants, and anorectics.9 More importantly, (R)-selegiline 6, a selective irreversible MAO-B inhibitor, is used in combination with l-DOPA or carbidopa for the treatment of early-stage Parkinson’s disease, depression, and senile dementia10 (Fig. 1). Although many strategies for the synthesis of either enantiomers of ephedrine 1–2 and amphetamine analogues 3–6 have been reported, most of them have mainly relied on racemic approaches,11 chiral pool starting materials,12 asymmetric hydrogenation,13 classical and kinetic resolutions,14 regioselective ring opening of a stable aziridinium ion and cis-3-aminooxetanes,15 double asymmetric induction approach,16 addition of nitromethane to the chiral chromium tricarbonyl complex of o-tolualdehyde,17 reduction of protected cyanohydrins,18 and biotransformations.19

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