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

26 April 2021, Version 1
Working Paper
This content is an early or alternative research output and has not been peer-reviewed by Cambridge University Press at the time of posting.

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.

Keywords

Enantioselective Cyclopropanation
dirhodium carboxylate compounds Rh 2
aryldiazoacetate

Supplementary materials

Title
Description
Actions
Title
Cyprop of aza-het-SI-ChemRXIV
Description
Actions

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Version History

Apr 26, 2021 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.14479593.v1
D O I: 10.26434/chemrxiv.14479593.v1 [opens in a new tab]

Funding

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

Author’s competing interest statement

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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