Kurimoto Yosuke, Nasu Teruhisa, Fujii Yuki, Asano Keisuke, Matsubara Seijiro
Department of Material Chemistry, Graduate School of Engineering , Kyoto University , Kyotodaigaku-Katsura, Nishikyo , Kyoto 615-8510 , Japan.
Org Lett. 2019 Apr 5;21(7):2156-2160. doi: 10.1021/acs.orglett.9b00462. Epub 2019 Mar 14.
The organocatalytic enantio- and diastereoselective cycloetherification of in situ generated cyanohydrins through the concomitant construction of three chiral carbon centers is reported. This protocol facilitates the concise synthesis of optically active tetrahydropyran derivatives, which are ubiquitous scaffolds found in various bioactive compounds, through the simultaneous construction of multiple bonds and stereogenic centers, including tetrasubstituted chiral carbons. The resulting products also contain multiple synthetically important functional groups, which expand their possible usefulness as chiral building blocks.
报道了通过原位生成的氰醇的有机催化对映选择性和非对映选择性环醚化反应，同时构建三个手性碳中心。该方法通过同时构建多个键和立体中心，包括四取代手性碳，促进了光学活性四氢吡喃衍生物的简洁合成，这些衍生物是各种生物活性化合物中普遍存在的骨架。所得产物还含有多个具有重要合成意义的官能团，这扩大了它们作为手性砌块的潜在用途。
