Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040 Linz, Austria.
Institute of Catalysis, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040 Linz, Austria.
Org Biomol Chem. 2022 Jan 26;20(4):824-830. doi: 10.1039/d1ob02235k.
Selenium-containing amino acids are valuable targets but methods for the stereoselective α-selenation of simple amino acid precursors are rare. We herein report the enantioselective electrophilic α-selenation of azlactones (masked α-amino acid derivatives) and isoxazolidin-5-ones (masked β-amino acids) using Cinchona alkaloids as easily accessible organocatalysts. A variety of differently substituted derivatives was accessed with reasonable levels of enantioselectivities and further studies concerning the stability and suitability of these compounds for further manipulations have been carried out as well.
含硒氨基酸是很有价值的目标，但对简单氨基酸前体进行立体选择性α-硒化的方法却很少见。我们在此报告了使用金鸡纳生物碱作为易得的有机催化剂，对氮丙啶酮（掩蔽的α-氨基酸衍生物）和异恶唑烷-5-酮（掩蔽的β-氨基酸）进行对映选择性亲电α-硒化。使用各种不同取代的衍生物，获得了合理的对映选择性水平，并且还进行了这些化合物的稳定性和进一步操作适用性的进一步研究。
