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

Author:
Vickerman, Kevin L., Stanley, Levi M.
Source:
Organic letters 2017 v.19 no.19 pp. 5054-5057
ISSN:
1523-7052
Subject:
catalysts, chemical reactions, chemical structure, enantioselective synthesis, nitrogen, organic compounds, oxygen, sulfur
Abstract:
Enantioselective synthesis of polycyclic nitrogen, oxygen, and sulfur heterocycles by rhodium-catalyzed intramolecular alkene hydroacylation is reported. The intramolecular hydroacylation reactions generate 1,4-dihydrocyclopenta[b]indol-3(2H)-ones and 3,4-dihydrocyclopenta[b]indol-1(2H)-one in moderate-to-high yields (65–99%) with good-to-excellent enantioselectivities (84–99% 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 (71–91% yield) with excellent enantioselectivities (97–99% ee).
Agid:
5826925