Department of Applied Chemistry, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
J Org Chem. 2022 Jul 1;87(13):8788-8795. doi: 10.1021/acs.joc.2c00753. Epub 2022 Jun 14.
A highly stereoselective (3 + 2) cycloaddition for the asymmetric synthesis of versatile cyclopentene compounds containing all-carbon quaternary stereocenters was developed. The phosphine-catalyzed reactions of alkynoates with α-alkylated electron-deficient alkenes bearing Oppolzer's camphorsultam showed high to excellent diastereoselectivities and perfect regioselectivities. The usefulness of this reaction was demonstrated in the concise formal synthesis of ()-(-)-puraquinonic acid.
发展了一种高对映选择性的（3 + 2）环加成反应，用于不对称合成含有全碳季碳立体中心的多功能环戊烯化合物。膦催化的炔酸酯与带有 Oppolzer 的樟脑磺内酰胺的α-烷基化缺电子烯烃的反应表现出高至优异的非对映选择性和完美的区域选择性。该反应的有用性在（）-（-）-puraquinonic 酸的简洁的形式合成中得到了证明。
