Asymmetric Double Hydroxycarbonylation of Alkynes to Chiral Succinic Acids Enabled by Palladium Relay Catalysis

Xiaolei Ji; Chaoren Shen; Xinxin Tian; Hongru Zhang; Xinyi Ren; Kaiwu Dong

doi:10.1002/anie.202204156

Asymmetric Double Hydroxycarbonylation of Alkynes to Chiral Succinic Acids Enabled by Palladium Relay Catalysis

Angew Chem Int Ed Engl. 2022 Jul 18;61(29):e202204156. doi: 10.1002/anie.202204156. Epub 2022 May 20.

Authors

Xiaolei Ji¹, Chaoren Shen¹, Xinxin Tian², Hongru Zhang¹, Xinyi Ren¹, Kaiwu Dong¹

Affiliations

¹ Shanghai Frontiers Science Center of Molecule Intelligent Syntheses, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, P. R. China.
² Institute of Molecular Science, Key Laboratory of Materials for Energy Conversion and Storage of Shanxi Province, Shanxi University, Taiyuan, 030006, P. R. China.

PMID: 35524419
DOI: 10.1002/anie.202204156

Abstract

A Pd-catalyzed asymmetric double hydroxycarbonylation of terminal alkynes was developed by using relay catalysis, providing a highly efficient route to chiral succinic acids (41 examples, 76-94 %, 94-99 % ee). Key to success was the combinatorial use of a Pd precursor with two distinct phosphine ligands in one pot. The synthetic utilities of this protocol were showcased in the facile synthesis of key intermediates for chiral pharmaceuticals.

Keywords: Alkynes; Carbonylation; Palladium; Relay Catalysis; Succinic Acid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes*
Catalysis
Molecular Structure
Palladium*
Stereoisomerism
Succinates

Substances

Alkynes
Succinates
Palladium