Sohail Muhammad, Kobayashi Keisuke, Tomoda Hiroshi, Ohshiro Taichi, Tanaka Fujie
Chemistry and Chemical Bioengineering Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna, Okinawa, 904-0495, Japan.
Microbial Chemistry and Medicinal Research Laboratories, Graduate School of Pharmaceutical Sciences, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo, 108-8641, Japan.
Chemistry. 2025 Apr 4;31(20):e202500140. doi: 10.1002/chem.202500140. Epub 2025 Feb 28.
In molecules with central chiral centers functionalized with aryl groups, the rotation of the single bond between the aryl group and the central chiral center may be hindered. Enantioconvergent alkylation reactions of racemic diastereomers to construct all-carbon quaternary stereocenters resulting in easing of the rotation around the axes are described. We demonstrated that the rotation of the bond between a central chiral carbon center and a dihydrobenzofuranone can be tuned by selection of either a tertiary carbon bearing a hydrogen or a quaternary carbon at the central chiral center. The products have the benefits of a central chiral center and a flexibly rotatable bond, which can facilitate interactions with other molecules.
在具有被芳基官能化的中心手性中心的分子中，芳基与中心手性中心之间单键的旋转可能会受到阻碍。本文描述了外消旋非对映异构体的对映收敛烷基化反应，以构建全碳季碳立体中心，从而使围绕轴的旋转变得容易。我们证明，通过选择中心手性中心上带有氢的叔碳或季碳，可以调节中心手性碳中心与二氢苯并呋喃酮之间键的旋转。这些产物具有中心手性中心和可灵活旋转键的优点，这有助于与其他分子发生相互作用。
