Catalytic, Enantioselective Synthesis of Polycyclic Nitrogen, Oxygen, and Sulfur Heterocycles via Rh-Catalyzed Alkene Hydroacylation

摘要

Enantioselective synthesis of polycyclic nitrogen, oxygen, and sulfur heterocycles by rhodium-catalyzed intramolecular alkene hydroacylation is reported. The intramolecular hydroacylation reactions generate 1,4-dihydrocyclo-penta[b]indol-3(2H)-ones and 3,4-dihydrocyclopenta[b]indol-1(2H)-one in moderate-to-high yields (6599%) with good-to-excellent enantioselectivities (8499% ee). The catalyst system also promotes alkene hydroacylation of 3-vinylfuran-, 3-vinylbenzothiophene-, and 3-vinylthiophene-2-carboxaldehydes to generate the corresponding ketone products in moderate-to-high yields (7191% yield) with excellent enantioselectivities (9799% ee).