Herein is reported the highly chemo- and regioselective synthesis of 3-vinyl-4-formyl and 3-vinyl-5-formylisoxazolidines from enals, hydroxylamines and dipolarophiles under thermal conditions. The reaction works in high yields for a large array of substituted enals and a variety of dipolarophiles. The reaction provides the respective isoxazolidines with high chemoselectivity, stereospecificity and diastereoselectivity without significant purification. The substitution pattern on the dipolarophile directs the regioselectivity of the reaction to provide either 3,4- or 3,5-substituted isoxazolidine isomers. This method provides access to a wide variety of highly substituted, stereochemically dense isoxazolidine scaffolds from the selective reaction of the three proposed components.

本文报道了在热条件下由烯醛，羟胺和亲二氟体高度化学合成和区域选择性合成3-乙烯基-4-甲酰基和3-乙烯基-5-甲酰基异恶唑烷。对于大量的取代的烯类化合物和各种双亲性试剂，该反应的收率很高。该反应为各自的异恶唑烷提供了高的化学选择性，立体特异性和非对映选择性，而没有明显的纯化。亲双极性体上的取代模式指导反应的区域选择性，以提供3,4-或3,5-取代的异恶唑烷异构体。该方法可从三种拟议组分的选择性反应中获得各种高度取代的，立体化学稠密的异恶唑烷骨架。