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Role of Additives to Overcome Limitations of Intermolecular Rhodium-Catalyzed Asymmetric Cyclopropanation

preprint
submitted on 24.04.2021, 17:40 and posted on 26.04.2021, 14:23 by Jack C. Sharland, Bo Wei, David J. Hardee, Timothy R Hodges, Wei Gong, Eric Voight, Huw Davies
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.

Funding

National Science Foundation ((CHE-1956154, CHE-1700982, CHE 1531620, CHE 1626172)

AbbVie, Inc

History

Email Address of Submitting Author

hmdavie@emory.edu

Institution

Emory University

Country

USA

ORCID For Submitting Author

0000-0001-6254-9398

Declaration of Conflict of Interest

The authors declare the following competing financial interests: H.M.L Davies is a named inventor on a patent entitled Dirhodium Catalyst Compositions and Synthetic Processes Related Thereto (US 8,974,428, issued 3/10/2015). D J. Hardee, T. R. Hodges, W. Gong, and E. A. Voight are employees of AbbVie. AbbVie contributed to the design, study conduct, and financial support for this research. AbbVie participated in the interpretation of data, review, and approval of the publication.

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