Enantioselective Electrochemical Lactonization Using Chiral Iodoarenes as Mediators

Wen-Chao Gao; Zi-Yue Xiong; Shafigh Pirhaghani; Thomas Wirth

doi:10.1055/s-0037-1610373

Synthesis, Inhaltsverzeichnis

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

,

Thomas Wirth *

School of Chemistry, Cardiff University, Park Place, Cardiff, CF10 3AT, UK eMail: wirth@cf.ac.uk

› Institutsangaben

Abstract

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Published as part of the 50 Years SYNTHESIS – Golden 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.

Key words

electrolysis - flow microreactors - hypervalent iodine - lactonization - stereoselective synthesis

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