Issue 9, 2024

Pd((R)-DTBM-SEGphos)Cl2-catalyzed kinetic resolution of tertiary propargylic alcohols

Abstract

We report here an asymmetric carboxylation reaction based on kinetic resolution of tertiary propargylic alcohols by identifying Pd((R)-DTBM-SEGphos)Cl2 as the pre-catalyst. A variety of optically active tertiary propargylic alcohols and tetrasubstituted 2,3-allenoic acids were obtained in good yields with excellent enantioselectivities. The salient features of this report include the use of readily available substrates, a readily available precatalyst, mild reaction conditions, remarkable functional group tolerance, gram-scale synthesis, and versatile synthetic transformations. Mass spectrometry experiments trapped some key intermediates, which revealed the mechanism.

Graphical abstract: Pd((R)-DTBM-SEGphos)Cl2-catalyzed kinetic resolution of tertiary propargylic alcohols

Supplementary files

Article information

Article type
Research Article
Submitted
13 Jan 2024
Accepted
28 Feb 2024
First published
01 Mar 2024
This article is Open Access
Creative Commons BY-NC license

Org. Chem. Front., 2024,11, 2477-2484

Pd((R)-DTBM-SEGphos)Cl2-catalyzed kinetic resolution of tertiary propargylic alcohols

J. Wang, W. Zheng, Y. Li, Y. Guo, H. Qian and S. Ma, Org. Chem. Front., 2024, 11, 2477 DOI: 10.1039/D4QO00082J

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