Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: Selective synthesis of lactones and lactams

…, DY Zhou, K Onitsuka, S Takahashi

Index: Yoneda, Eiji; Zhang, Shi-Wei; Zhou, Da-Yang; Onitsuka, Kiyotaka; Takahashi, Shigetoshi Journal of Organic Chemistry, 2003 , vol. 68, # 22 p. 8571 - 8576

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Citation Number: 46

Abstract

Allenyl alcohols such as 4-hydroxybuta-1, 2-dienes and 5-hydroxypenta-1, 2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five-and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1, 2-dines are also cyclocarbonylated to give γ- lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate ...