Jun Chen, Zhan Shi, Chunyu Li and Ping Lu
Chem. Sci., 2021,12, 10598-10604
DOI:
10.1039/D1SC02119B,
Edge Article
We report here a sequential enantioselective reduction/C–H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C–H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol.