论文类型：期刊论文
发表刊物：ADVANCED SYNTHESIS & CATALYSIS
收录刊物：SCIE
卷号：360
期号：4
页面范围：664-669
ISSN号：1615-4150
关键字：Friedel-Crafts reaction; Chiral phosphoric acid; Indole; Enantioselectivity; Ketimino ester
摘要：Through a hydrogen bonding guided substrate modification strategy, we have developed a chiral phosphoric acid catalyzed highly enantiose-lective Friedel-Crafts reaction of N-protected 4-aminoindoles with beta,gamma-unsaturated alpha-ketimino esters. The mechanism and origins of the enantioselectivity of this process are indentified using DFT calculations. Both the experimental and calculation results indicated that the NH moiety at the indole C4 position is essential for the stereocontrol of this reaction. To further examine the potential usefulness of this method, gram scale synthesis and derivatizations of one of the products were also carried out.