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

Jie Wang; Wei-Feng Zheng; Yuling Li; Yin-Long Guo; Hui Qian; Shengming Ma

doi:10.1039/D4QO00082J

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

Jie Wang,

‡^a Wei-Feng Zheng,‡^a Yuling Li,^b Yin-Long Guo,

*^b Hui Qian

*^a and Shengming Ma

^ab

Author affiliations

* Corresponding authors

^a Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. China
E-mail: qian_hui@fudan.edu.cn

^b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P. R. China
E-mail: ylguo@sioc.ac.cn

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.

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Article information

DOI: https://doi.org/10.1039/D4QO00082J
Article type: Research Article
Submitted: 13 Jan 2024
Accepted: 28 Feb 2024
First published: 01 Mar 2024
This article is Open Access

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

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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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