Palladium/H+-cocatalyzed kinetic resolution of tertiary propargylic alcohols

Wanli Zhang; Shengming Ma

doi:10.1039/C8CC01949E

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Palladium/H⁺-cocatalyzed kinetic resolution of tertiary propargylic alcohols†

Wanli Zhang^a and Shengming Ma

*^bc

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory of Green Chemistry and Chemical Process, College of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. China

^b Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai 200433, P. R. China

^c 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: masm@sioc.ac.cn

Abstract

A new approach to not-readily-available optically active tertiary propargylic alcohols through palladium/H⁺-cocatalyzed carboxylation of racemic tertiary propargylic alcohols with CO and MeOH has been described. Both enantiomers can be obtained with no less than 90% ee utilizing (R) or (S)-DTBM-Segphos. Various transformations of the optically active alcohols have been demonstrated.

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Article information

DOI: https://doi.org/10.1039/C8CC01949E
Article type: Communication
Submitted: 11 Mar 2018
Accepted: 09 May 2018
First published: 11 May 2018

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Chem. Commun., 2018,54, 6064-6067

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Palladium/H⁺-cocatalyzed kinetic resolution of tertiary propargylic alcohols

W. Zhang and S. Ma, Chem. Commun., 2018, 54, 6064 DOI: 10.1039/C8CC01949E

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