American Chemical Society
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A Proline-Squaraine Ligand Framework (Pro-SqEB) for Stereoselective Rhodium(II)-Catalyzed Cyclopropanations

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journal contribution
posted on 2023-11-08, 19:41 authored by Emily P. Bacher, Raïssa Twiringiyimana, Kevin X. Rodriguez, Renita A. Wilson, Alexandra K. Bodnar, Ryan O’Connell, Tiffany A. Toni, Kaitlyn E. Eckert, Olaf Wiest, Brandon L. Ashfeld
A proline-squaraine ligand (Pro-SqEB) that demonstrates high levels of stereoselectivity in olefin cyclopropanations when anchored to a Rh2II scaffold is introduced. High yields and enantioselectivities were achieved in the cyclopropanation of alkenes with diazo compounds in the presence of Rh2(Pro-SqEB)4. Notably, the unique electronic and steric design of this catalyst enabled the use of polar solvents that are otherwise incompatible with most RhII complexes.