Synfacts 2021; 17(06): 0643
DOI: 10.1055/s-0040-1720515
Metals in Synthesis

Enantioselective C–H Rutheniation for the Preparation of Tetrahydrocarbazoles and Cyclohepta[b]indoles

Contributor(s):
Paul Knochel
,
Alexander Kremsmair
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.
 

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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Publication History

Publication Date:
18 May 2021 (online)

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