CC BY-ND-NC 4.0 · Synthesis 2019; 51(01): 276-284
DOI: 10.1055/s-0037-1610373
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Enantioselective Electrochemical Lactonization Using Chiral Iodoarenes as Mediators

Wen-Chao Gao
,
Zi-Yue Xiong
,
Shafigh Pirhaghani
,
School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK   Email: wirth@cf.ac.uk
› Author Affiliations
This work was supported by the China Scholarship Council (No. 201608140185). Support from Cardiff University and Taiyuan University of Technology is gratefully acknowledged.
Further Information

Publication History

Received: 07 September 2018

Accepted after revision: 04 October 2018

Publication Date:
25 October 2018 (eFirst)

Published as part of the 50 Years SYNTHESISGolden Anniversary Issue

Abstract

The enantioselective electrochemical lactonization of diketo acid derivatives using chiral iodoarenes as redox mediators is reported for the first time. Good to high stereoselectivities are observed in the lactonization and also in intermolecular α-alkoxylations of diketo ester derivatives. This enantioselective process was then adapted to an electrochemical flow microreactor where only small amounts of supporting electrolyte were necessary.

Supporting Information

 
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