| 主权项 |
1. A method of stereoselective or regioselective synthesis of a compound, comprising:
converting a substituted β amino alcohol to a substituted aziridinium ion selected from:where: Y is a non-nucleophilic counter anion or a leaving group comprising halide, perchlorate, tetrafluoroborate, hexafluoroantimonate, mesylate, triflate, carbonate, nitrate, phthalimide, or succinimide; each of R1-4 independently is or includes hydrogen, carboxyalkyl, alkylamido, alkyl, allyl, benzyl, benzyloxyalkyl, cycloalkyl, heterocyclyl, alkoxy, hydroxyalkyl, aryl, CH2Ar, aryloxy, hydroxyaryl, heteroaryl, phenyl, vinyl, alkynyl, alkenyl, substituted carbonyl, halo, haloalkyl, nitrile, oxo, substituted oxo, substituted silyl, thiol, benzhydryl, silyl, substituted carboxyl, hydroxyalkyl, aminoalkyl, alkoxycarbonyl, alkylamido, furannylalkyl, alkylthioalkyl, arylhydroxyalkyl, indanyl, indolylalkyl, naphthylalkyl, imidazolylalkyl, pyridiylalkyl, phthalimidyl, maleimidyl, benzothiophenylalkyl, thiophenylalkyl, thioalkyl, thioaryl, thiobenzyl, hydroxy, hydroxyalkyl, aminoalkyl, tosyl, nosyl, a protected amine, carboxyl, carboxyalkyloxy, amino, carboxylic acid, holoalkylamido, aldehyde, alkylamino, amido, trityl, tert-butyloxycarbonyl, carbobenzyloxy, acetyl, dimethoxybenzyl, p-methoxybenzyl, an amide containing group, a thioamide containing group, an amino acid-containing group, an ester containing group, an amine protecting group, any two vicinal carbons of R1 and R2 together form a fused ring —(CH2)n—, any two germinal carbons, R1 and R2 are bonded together and form a spiro ring, any of R1-5 is or attached to chiral carbon, or is one of:where n=1-10 and X is or includes hydrogen, halo, cyano, alkyl, aryl, hydroxyl, nitro, amino, alkylamino, dialkylamino, substituted amine, substituted carbonyl, isocyanate, cyanate ester, protected amine, protected hydroxyl, protected carboxyl, boronic acid, borinic acid, borinate ester, triflate, silyl, substituted silyl, thiocyano, isothiocyano, alkoxy, aryloxy, carboxyl, carboxylic acid, carboxyalkyl, carboxyalkyloxy, ester, amido, aldehydo, alkylamido, holoalkylamido, an ester containing group, an carbonyl containing group, a boron containing group, a tin containing group, an amide containing group, a thioamide containing group, or an amino acid-containing group, and R3-4 can also be:where: n=1-3; Ar is an aromatic ring bonded to one of the n carbons; R5 is as defined for R1-R4; and R′ independently is OH, NH2, NR″2, or OR″, wherein R″ independently is alkyl, tert-butyl, allyl, benzyl, CH2Ar, silyl, trityl, an amine protecting group, a carboxyl protecting group, or a hydroxyl protecting group, and Ar in CH2Ar represents an aromatic ring; and
stereoselectively or regioselectively reacting the aziridinium ion in a nucleophilic ring opening reaction to obtain the compound. |
