Boxer Matthew B, Yamamoto Hisashi
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
Nat Protoc. 2006;1(5):2434-8. doi: 10.1038/nprot.2006.389.
The synthesis of the acetaldehyde-derived tris(trimethylsilyl)silyl (super silyl) enol ether is described, as well as its use in the high-yielding aldehyde cross-aldol reaction. The super silyl enol ether shows unprecedented reactivity in giving the 1:1 adduct in very high yield. This reaction is catalyzed by 0.05 mol% of the Brønsted acid triflimide (HNTf2) and is complete within 15 min, making the protocol very attractive for large-scale synthesis.
描述了乙醛衍生的三(三甲基硅基)硅基(超级硅基)烯醇醚的合成及其在高产率醛交叉羟醛反应中的应用。超级硅基烯醇醚在以非常高的产率生成1:1加合物方面表现出前所未有的反应活性。该反应由0.05 mol%的布朗斯特酸三氟甲磺酰亚胺(HNTf2)催化,15分钟内完成,这使得该方法对大规模合成非常有吸引力。