Role of Additives to Overcome Limitations of Intermolecular Rhodium-Catalyzed Asymmetric Cyclopropanation
Year: 2021
Type: preprint
Abstract: This study describes general methods for the enantioselective syntheses of disubstituted cyclopropane carboxylates including substitution patterns or heterocycle functionality previously observed as significant limitations. The key step is the dirhodium tetracarboxylate-catalyzed asymmetric cyclopropanation of vinyl arenes with aryl- or heteroaryldiazoacetates. The reactions are highly diastereoselective and high asymmetric induction could be achieved using either ( R )-pantolactone as a chiral auxiliary or chiral dirhodium tetracarboxylate catalysts.
Source: ChemRxiv
Authors: Jack C. Sharland, Bo Wei, David J. Hardee, Timothy R Hodges, Wei Gong, Eric Voight, Huw Davies
Institutions: Emory University, AbbVie (United States)
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: G2027168600, G236029928, MRI: Acquisition of a 600 MHz NMR Spectrometer for Chemistry, G3085896116, MRI: Acquisition of a High Intensity Single Crystal X-ray Diffractometer, G4421890870, G454325550, New Catalysts to Expand the Scope of Donor/Acceptor Carbenes, G614714729, G7730288108, NSF Center for Selective CH Functionalization
OpenAlex ID: W3161083298