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Enantioselective Ruthenium-Catalyzed C–H Alkylations by a Chiral Carboxylic Acid with Attractive Dispersive Interactions

Dhawa, Uttam ; Connon, Robert ; Oliveira, João C. A ; Steinbock, Ralf ; Ackermann, Lutz

Organic letters, 2021-04, Vol.23 (7), p.2760-2765 [Periódico revisado por pares]

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Título:
Enantioselective Ruthenium-Catalyzed C–H Alkylations by a Chiral Carboxylic Acid with Attractive Dispersive Interactions
Autor: Dhawa, Uttam ; Connon, Robert ; Oliveira, João C. A ; Steinbock, Ralf ; Ackermann, Lutz
É parte de: Organic letters, 2021-04, Vol.23 (7), p.2760-2765
Notas: ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
Descrição: Asymmetric ruthenium-catalyzed C–H alkylations were enabled by a chiral C2-symmetric carboxylic acid. The mild cooperative ruthenium(II) catalysis set the stage for the assembly of chiral tetrahydrocarbazoles and cyclohepta[b]indoles with high levels of enantioselectivity at room temperature. Mechanistic studies by experiment and computation identified a fast C–H ruthenation, along with a rate- and enantio-determining proto-demetalation. The asymmetric induction was governed by weak attractive secondary dispersion interactions as found in NCI analysis of the key transition states.
Editor: United States: American Chemical Society
Idioma: Inglês

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