Wada Yuuki, Murata Ryuichi, 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. 2020 Jun 19;22(12):4710-4715. doi: 10.1021/acs.orglett.0c01501. Epub 2020 Jun 3.
The organocatalytic enantio- and diastereoselective cycloetherification of 1,3-cyclohexanedione-bearing enones involving the in situ generation of chiral cyanohydrins was developed. This transformation offers the first catalytic asymmetric approach to oxadecalin derivatives containing contiguous tetrasubstituted chiral carbons at the bridge heads of the fused ring systems. Depending on substituents, both - and -decalin-type scaffolds were synthesized with good to excellent stereoselectivities, and a range of functional groups accumulated on the chiral quaternary carbon moieties of the -oxadecalin derivatives.
开发了一种有机催化的对映和非对映选择性环醚化反应，该反应涉及含1,3 - 环己二酮的烯酮原位生成手性氰醇。这种转化为稠环体系桥头含有连续四取代手性碳的氧杂十氢化萘衍生物提供了第一种催化不对称方法。根据取代基的不同，合成了具有良好至优异立体选择性的α-和β-十氢化萘型骨架，并且在α-氧杂十氢化萘衍生物的手性季碳部分积累了一系列官能团。
