Asymmetric and Nonasymmetric Addition of RLi and RMgX to 3-Methoxynaphthalen-2-yl Oxazolines and Imines. An Approach to Substituted 2-Tetralones
作者:Sergei V. Kolotuchin、A. I. Meyers
DOI:10.1021/jo991727c
日期:2000.5.1
displacement of the 3-methoxy group with organolithium reagents and instead afforded dihydronaphthalenes 9 and 14 in 30-95% yield. Dihydronaphthalenes 9 (racemic) and 14 (nonracemic) were easily converted into the corresponding aldehydes 15. Alternatively, aldehydes 15 were prepared via tandem addition of Grignard reagents to imines 17 in 50-65% yield. Aldehydes 15 served as precursors to 3,3, 4-trisubstituted
手性和非手性3-甲氧基萘-2-基恶唑啉4a,b不能用有机锂试剂进行3-甲氧基的芳香亲核取代,而是以30-95%的收率得到二氢萘9和14。二氢萘9(外消旋)和14(非外消旋)很容易转化为相应的醛15。或者,通过将格氏试剂串联添加到亚胺17上以50-65%的收率制备醛15。醛15为3,3,4-三取代的2-四氢萘酮16的前体。使用氯甲酸甲酯捕获17f和i-PrMgCl衍生的氮杂烯酸酯,收率为65%,提供了一种通用的合成中间体23,可用于获取具有各种取代方式的4-烷基,3,4-二烷基,3,4-二取代和3,3,4-三取代的2-四氢萘酮。