Palladium-catalyzed asymmetric allenylic alkylation: construction of multiple chiral thiochromanone derivatives
Lixia Liu, Yu-Qing Bai, Xiang Li, Chang‐Bin Yu, Yong‐Gui Zhou
Abstract
The development of a new strategy for the construction of chiral cyclic sulfide-containing multiple stereogenic centers is highly desirable. Herein, by the combination of base-promoted retro-sulfa-Michael addition and palladium-catalyzed asymmetric allenylic alkylation, the streamlined synthesis of chiral thiochromanones containing two central chiralities (including a quaternary stereogenic center) and an axial chirality (allene unit) was successfully realized with up to 98% yield, 49.0 : 1 dr and >99% ee.
Topics & Concepts
PalladiumAlkylationCatalysisTsuji–Trost reactionChemistryCombinatorial chemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsSulfur-Based Synthesis Techniques