| 摘要 |
In certain embodiments, the present invention relates to methods for asymmetric Friedel-Crafts alkylation catalyzed by bifunctional cinchona alkaloids. In certain embodiments, the catalyst is a 6′-OH cinchona alkaloid. In certain embodiments, the electrophile is an α-ketoester or aldehyde. In certain embodiments, the nucleophile is an aromatic heterocycle. In certain embodiments, the nucleophile is an aromatic N-containing heterocycle. In certain embodiments, the nucleophile is an indole. In certain embodiments, the methods of the invention are relatively insensitive to concentration, temperature, air and moisture. |
| 主权项 |
1. A method of preparing a chiral, non-racemic alcohol from a prochiral aldehyde or prochiral ketone, comprising the step of:
reacting a prochiral aldehyde or prochiral ketone with an aromatic compound in the presence of a catalyst; thereby producing a chiral, non-racemic alcohol; wherein said aromatic compound is selected from the group consisting of D is H, alkyl, aralkyl or acyl; E is, independently for each occurrence, H, alkyl, alkenyl, aryl, cycloalkyl, aralkyl, heteroalkyl, halogen, hydroxy, cyano, amino, acyl, alkoxyl, nitro, thiol, amine, amido, phosphonate, phosphine, carboxyl, sulfonyl, ketone, aldehyde or ester; said chiral, non-racemic alcohol has an enantiomeric excess or diastereomeric excess greater than about 70%; and said catalyst is |
