Wu Zhiyong, Lebœuf David, Retailleau Pascal, Gandon Vincent, Marinetti Angela, Voituriez Arnaud
Institut de Chimie des Substances Naturelles, CNRS UPR 2301, Univ. Paris-Sud, Université Paris-Saclay, 1, av. de la Terrasse, 91198 Gif-sur-Yvette, France.
Institut de Chimie Moléculaire et des Matériaux d'Orsay, CNRS UMR 8182, Univ. Paris-Sud, Université Paris-Saclay, bâtiment 420, 91405 Orsay Cedex, France.
Chem Commun (Camb). 2017 Jul 4;53(52):7026-7029. doi: 10.1039/c7cc03234j. Epub 2017 Jun 14.
A gold(i)-catalyzed cycloisomerization/ring expansion sequence allows the highly enantioselective synthesis of 2-oxocyclobutylcyclopentane derivatives from cyclopropyl-substituted enynes. The bimetallic [(R)-MeO-DTBM-BIPHEP-(AuCl)] complex was found to be the best precatalyst, affording the desired cyclobutanones in high yields and enantioselectivities (up to 99% ee). The usefulness of the method was further demonstrated by preparing the tricyclic core scaffold of russujaponol D.
金（I）催化的环异构化/扩环反应序列可实现从环丙基取代的烯炔高度对映选择性合成2-氧代环丁基环戊烷衍生物。发现双金属[(R)-MeO-DTBM-BIPHEP-(AuCl)]配合物是最佳的预催化剂，能以高收率和对映选择性（高达99% ee）得到所需的环丁酮。通过制备紫苏醇D的三环核心骨架进一步证明了该方法的实用性。
