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Synfacts 2021; 17(06): 0643
DOI: 10.1055/s-0040-1720515
DOI: 10.1055/s-0040-1720515
Metals in Synthesis
Enantioselective C–H Rutheniation for the Preparation of Tetrahydrocarbazoles and Cyclohepta[b]indoles
Dhawa U,
Connon R,
Oliveira JC. A,
Steinbock R,
Ackermann L.
*
Georg-August-Universität Göttingen, Germany
Enantioselective Ruthenium-Catalyzed C–H Alkylations by a Chiral Carboxylic Acid with Attractive Dispersive Interactions.
Org. Lett. 2021;
23: 2760-2765
DOI: 10.1021/acs.orglett.1c00615
Enantioselective Ruthenium-Catalyzed C–H Alkylations by a Chiral Carboxylic Acid with Attractive Dispersive Interactions.
Org. Lett. 2021;
23: 2760-2765
DOI: 10.1021/acs.orglett.1c00615
Significance
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.
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Comment
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.
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Publikationsverlauf
Artikel online veröffentlicht:
18. Mai 2021
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