ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
2 files

Gold-Catalyzed Carboamination of Allenes by Tertiary Amines Proceeding with Benzylic Group Migration

preprint
submitted on 23.12.2020, 11:30 and posted on 24.12.2020, 06:29 by Pierre Milcendeau, Vincent Gandon, Xavier Guinchard

Tertiary amines bearing a benzyl-type group (CH2Ar) undergo Au(I)-catalyzed intramolecular addition to allenes. A formal 1,3-transfer of the CH2Ar group takes place during the cyclization. As demonstrated by both experimental and DFT studies, these unprecedented intramolecular carboaminations involve two consecutive [3,3] rearrangements via a dearomatized intermediate. Because of the poor stability of the enamine products, protocols were developed to convert them in situ to more stable polycyclic chiral compounds.

Funding

CHARMMMAT Laboratory of Excellence (ANR-11-LABX0039)

HPC resources of CINES under the allocation 2020-A0070810977 made by GENCI.

History

Email Address of Submitting Author

xavier.guinchard@cnrs.fr

Institution

ICSN CNRS

Country

France

ORCID For Submitting Author

0000-0003-2353-8236

Declaration of Conflict of Interest

no conflict of interest

Exports

Logo branding

Exports