不对称异硫脲催化的对醌甲基化物与联烯酸酯的(4 + 2)环加成反应。

Scheucher Anna, Gross Christoph, Piringer Magdalena, Novacek Johanna, Ofial Armin R, Waser Mario

Institute of Organic Chemistry, Johannes Kepler University Linz, Altenbergerstrasse 69, 4040 Linz, Austria.

Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, 81377 München, Germany.

Org Biomol Chem. 2025 Jan 22;23(4):827-834. doi: 10.1039/d4ob01855a.

Chiral isochalcogenoureas ( isothioureas and isoselenoureas) catalyse the asymmetric (4 + 2)-cycloaddition of various allenoates with -quinone methides. This approach provides straightforward access to different chromane derivatives with high enantioselectivities, good yields, and control of the configuration of the exocyclic double bond. Furthermore, some of the novel -quinone methides used herein were successfully integrated into the Mayr reactivity scale by determining their electrophilicity parameter.

手性异硫属脲（异硫脲和异硒脲）催化各种烯丙酸酯与醌甲基化物的不对称（4+2）环加成反应。这种方法为直接获得具有高对映选择性、良好产率且能控制环外双键构型的不同色满衍生物提供了途径。此外，本文中使用的一些新型醌甲基化物通过测定其亲电参数成功地纳入了迈尔反应活性标度。