Patent ID: 6258960
Filing Date: 2001-07-10
Classification: C07D,C07F

Abstract:
A process for preparing a chiral cis-aziridine of the formula (IIIa) or (IIIb) ##STR29##where:R.sup.1 is hydrogen, substituted carbonyl, halo, secondary amino, tertiary amino, nitrile, nitro, alkyl, alkenyl, alkynyl, alkoxy, aryl or heterocyclyl groups;R.sup.2 is hydrogen, hydroxyl, amino, oxo, substituted carbonyl, thiol, halo, nitrile, nitro, alkyl, alkenyl, alkynyl, alkoxy, aryl or heterocyclyl groups;R.sup.3 is hydrogen, substituted carbonyl, halo, secondary amino, tertiary amino, nitrile, nitro, alkyl, alkenyl, alkynyl, alkoxy, aryl or heterocyclyl groups;R.sup.4 and R.sup.5 are each independently hydrogen, secondary amino, tertiary amino, substituted oxo, substituted carbonyl, thiol, halo, nitrile, nitro, substituted silyl, alkyl, alkenyl, alkynyl, alkoxy, aryl or heterocyclyl groups;comprising reacting an imine of the formula (I): ##STR30##where R.sup.1, R.sup.2 and R.sup.3 are defined above, with a diazo compound of the formula (II): ##STR31##where R.sup.4 and R.sup.5 are defined above,in the presence of a chiral vaulted biaryl-Lewis acid complex of the formula (IVa) or (IVb): ##STR32##where X is N, O or S;R.sup.6 and R.sup.7 are each independently an alkyl, aryl or heterocycyl group; andR.sup.8, R.sup.9, R.sup.10, R.sup.11, R.sup.12, and R.sup.13 are, each independently, hydrogen, alkyl, aryl, and heterocyclyl; orwhere R.sup.6 and R.sup.8, R.sup.7 and R.sup.11, R.sup.9 and R.sup.10, and R.sup.12 and R.sup.13 may, each pair independently, form a fused aliphatic or aromatic ring;wherein cis-aziridine (IIIa) is obtained when catalyst (IVa) is employed or wherein cis-aziridine (IIIb) is obtained when catalyst (IVb) is employed.