钌（II）卟啉催化α-重氮酮的串联羰基叶立德形成及1,3-偶极环加成反应。

Ruthenium(II) porphyrin catalyzed tandem carbonyl ylide formation and 1,3-dipolar cycloaddition reactions of alpha-diazo ketones.

作者信息

Zhou Cong-Ying, Yu Wing-Yiu, Che Chi-Ming

机构信息

Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drug Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong.

出版信息

Org Lett. 2002 Sep 19;4(19):3235-8. doi: 10.1021/ol0201254.

DOI:10.1021/ol0201254

PMID:12227757

Abstract

[reaction: see text] The ruthenium porphyrin-catalyzed reactions of diazo ketones with pi-unsaturated compounds via carbonyl ylide formation/cycloaddition cascade exhibit product yields and selectivities comparable to the analogous reactions with dirhodium carboxylates as catalysts. By grafting a ruthenium porphyrin on poly(ethylene glycol) (Zhang, J.-L.; Che, C.-M. Org. Lett. 2002, 4, 1911), a recyclable catalytic system is developed with over 5700 product turnovers attained for the reaction of 1-diazo-2,5-hexanedione with dimethyl acetylenedicarboxylate.

摘要

[反应：见正文] 钌卟啉催化重氮酮与π-不饱和化合物通过羰基叶立德形成/环加成串联反应，其产物产率和选择性与以二铑羧酸盐为催化剂的类似反应相当。通过将钌卟啉接枝到聚乙二醇上（张，J.-L.；车，C.-M. 《有机快报》2002年，4，1911），开发了一种可循环催化体系，对于1-重氮-2,5-己二酮与二甲基乙炔二羧酸酯的反应，产物周转数超过5700。