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Enantioselective C–H Rutheniation for the Preparation of Tetrahydrocarbazoles and Cyclohepta[b]indoles
Enantioselective Ruthenium-Catalyzed C–H Alkylations by a Chiral Carboxylic Acid with Attractive Dispersive Interactions.
Org. Lett. 2021;
Ackermann and co-workers report a cooperative ruthenium(II) and chiral Lewis acid catalysis protocol for the enantioselective C–H alkylation of indole derivatives, affording tetrahydrocarbazoles and cyclohepta[b]indoles in high yields and good enantioselectivities.
Mechanistic experiments and computations found that a fast C–H rutheniation formed intermediate A, which formed racemic intermediate B upon coordination and migratory insertion. Then the enantio-determining proto-demetalation took place, affording the desired product.
18 May 2021 (online)
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