Issue 5, 2022

Chiral phosphoric acid-catalyzed regio- and enantioselective reactions of functionalized propargylic alcohols

Abstract

Propargylic alcohols have been known as useful substrates in a wide range of asymmetric reactions. In particular, chiral phosphoric acid (CPA) catalyzed reactions of functionalized propargylic alcohols have opened robust access to axially chiral tetrasubstituted allenes and their related derivatives. However, these types of propargylic alcohols have been essentially limited to the structures that could form quinone methides or methide indoles. Here, we expand the scope of propargylic alcohols and the power of CPA catalysis. With the established system, racemic 3-alkynyl-3-hydroxyisoindolinones reacted efficiently to form diverse spirocyclic heterocycles with high enantioselectivity. Regiodivergence was also observed with different indole nucleophiles. Importantly, the key covalently bonded CPA adduct was isolated, characterized, and further confirmed to be chemically competent, and a possible covalent activation mode was proposed accordingly.

Graphical abstract: Chiral phosphoric acid-catalyzed regio- and enantioselective reactions of functionalized propargylic alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
15 Dez 2021
Accepted
11 Jän 2022
First published
12 Jän 2022

Org. Chem. Front., 2022,9, 1234-1240

Chiral phosphoric acid-catalyzed regio- and enantioselective reactions of functionalized propargylic alcohols

C. Qian, M. Liu, J. Sun and P. Li, Org. Chem. Front., 2022, 9, 1234 DOI: 10.1039/D1QO01864G

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