State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, People's Republic of China.
Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, 1088 Xueyuan Boulevard, Shenzhen 518055, People's Republic of China.
J Am Chem Soc. 2021 Jun 16;143(23):8583-8589. doi: 10.1021/jacs.1c03498. Epub 2021 Jun 1.
A one-pot rhodium-catalyzed C-H functionalization/organocatalyzed oxa-Michael addition cascade reaction has been developed. This methodology enables the stereodivergent synthesis of diverse 2,3-disubstituted dihydrobenzofurans with broad functional group compatibility in good yields with high levels of stereoselectivity under exceptionally mild conditions. The full complement of stereoisomers of chiral 2,3-disubstituted dihydrobenzofurans and 3,4-disubstituted isochromans could be accessed at will by appropriate permutations of the two chiral catalysts. The current work provides a rare example of two chiral catalysts independently controlling two contiguous stereogenic centers subsequently via a two-step reaction in a single operation.
发展了一种一锅铑催化的 C-H 官能化/有机催化的氧杂-Michael 加成级联反应。该方法能够在极其温和的条件下，以优异的立体选择性和高收率，通过广泛的官能团兼容性，立体发散地合成各种 2,3-二取代二氢苯并呋喃。通过适当排列两种手性催化剂，可以随意获得手性 2,3-二取代二氢苯并呋喃和 3,4-二取代异苯并呋喃的全部立体异构体。目前的工作提供了一个罕见的例子，即两个手性催化剂通过两步反应在单个操作中独立控制两个连续的立体中心。
