Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109-1055, USA.
Org Lett. 2011 Sep 2;13(17):4728-31. doi: 10.1021/ol2020048. Epub 2011 Aug 3.
The stereoselective synthesis of 2,4- and 2,5-disubstituted 1,3-oxazolidines is accomplished via Pd-catalyzed carboamination of O-vinyl-1,2-amino alcohol derivatives. The transformations generate cis-disubstituted products with good to excellent diastereoselectivity, and enantiomerically enriched substrates are converted without loss of optical purity. In addition to yielding synthetically useful products that are difficult to generate with existing methods, these transformations illustrate that electron-rich enol ethers are viable substrates for alkene carboamination processes.
通过 Pd 催化的 O-乙烯基-1,2-氨基醇衍生物的碳氨化反应，实现了 2,4-和 2,5-取代的 1,3-恶唑烷的立体选择性合成。这些转化生成了具有良好至优秀的非对映选择性的顺式二取代产物，并且对映体富集的底物在不损失光学纯度的情况下转化。除了生成现有方法难以生成的具有合成用途的产物外，这些转化还表明富电子烯醇醚是烯烃碳氨化过程的可行底物。
