Copper mediated, heterogeneous, enantioselective intramolecular Buchner reactions of α-diazoketones using continuous flow processing

• DC Crowley^†
• D Lynch^†
• AR Maguire^‡

• ^† School of Chemistry, Analytical and Biological Chemistry Research Facility, University College Cork, Cork T12 K8AF, Ireland
• ^‡ School of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre, University College Cork, Cork T12 K8AF, Ireland

Enantioselective intramolecular Buchner reactions of α-diazoketones can be effected using heterogeneous copper–bis(oxazoline) catalysts in batch or using continuous flow processing in up to 83% ee. The catalyst can be reused up to 7 times without loss of activity. For α-diazoketones 3 and 4, the enantioselection achieved in flow with the immobilized catalyst was comparable with the standard homogeneous catalyzed process.

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