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铜介导的、多相的、对映选择性的α-重氮酮的 Buchner 分子内环化反应在连续流工艺中的应用。

Copper-Mediated, Heterogeneous, Enantioselective Intramolecular Buchner Reactions of α-Diazoketones Using Continuous Flow Processing.

机构信息

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.

出版信息

J Org Chem. 2018 Apr 6;83(7):3794-3805. doi: 10.1021/acs.joc.8b00147. Epub 2018 Mar 28.

DOI:10.1021/acs.joc.8b00147
PMID:29543458
Abstract

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.

摘要

使用非均相铜-双(恶唑啉)催化剂,α-重氮酮的对映选择性分子内 Buchner 反应可以在分批或连续流处理中进行,ee 值高达 83%。催化剂可重复使用 7 次而不损失活性。对于 α-重氮酮 3 和 4,固定化催化剂在流动相中获得的对映选择性与标准均相催化过程相当。

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