Neutral coordinate-organocatalysts in organic synthesis: Allylation of acylhydrazones with allyltrichlorosilanes

被引:97
作者
Kobayashi, S [1 ]
Sugiura, M [1 ]
Ogawa, C [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
allylation; amides; C-C bond formation; hydrazones; organic catalysis; phosphane oxides; sulfoxides;
D O I
10.1002/adsc.200404101
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
N,N-Dimethylformamide (DMF), sulfoxides, and phosphine oxides, etc., which are neutral, uncharged molecules and coordinate to silicon atoms of organosilicon reagents to activate nucleophilic addition, are defined as neutral coordinate-organocatalysts (NCOs). In the presence of NCOs, allylation reactions of acylhydrazones, useful imine surrogates, using allyltrichlorosilanes proceed smoothly to afford the synthetically useful racemic and non-racemic homoallylic amine derivatives in high yields with high diastereoselectivities.
引用
收藏
页码:1023 / 1034
页数:12
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