Issue 12, 2022

Secondary-sphere modification in proline catalysis: old friend, new connection

Abstract

In this work, we exploit our strategy of in situ secondary-sphere modification of organocatalysts to improve the reactivity and selectivity of amino catalysts. Herein, the carboxylic acid moiety of proline was targeted as a site for modification under catalytic reaction conditions with boronic acids. Intermolecular aldol reactions between aromatic aldehydes and cyclopentanone were selected as a proof-of-concept because cyclopentanone as an aldol donor was often associated with decreased selectivity compared to its 6-membered ring analog, hexanone. Our secondary-sphere modification strategy, using naturally occurring L-proline amino acid, enabled reactions at room temperature with high levels of diastereo- and enantio-selectivity and short reaction times. NMR and HR-MS studies shed light on the nature of the catalyst structure and on the role of water in our reactions.

Graphical abstract: Secondary-sphere modification in proline catalysis: old friend, new connection

Supplementary files

Article information

Article type
Communication
Submitted
03 Nhl 2021
Accepted
23 N’w 2021
First published
23 N’w 2021

Chem. Commun., 2022,58, 1950-1953

Secondary-sphere modification in proline catalysis: old friend, new connection

I. Domb, D. M. Lustosa and A. Milo, Chem. Commun., 2022, 58, 1950 DOI: 10.1039/D1CC05589E

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