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 10月 2021
Accepted
23 12月 2021
First published
23 12月 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements