標題: Assembly of Dimethyl Acetylenedicarboxylate and Phosphanes with Aldehydes Leading to gamma-Lactones Bearing alpha-Phosphorus Ylides as Wittig Reagents
作者: Deng, Jie-Cheng
Chan, Fu-Wei
Kuo, Chih-Wei
Cheng, Chun-An
Huang, Chien-Yu
Chuang, Shih-Ching
應用化學系
Department of Applied Chemistry
關鍵字: Lactones;Phosphanes;Ylides;Wittig reactions;Multicomponent reactions
公開日期: 1-十月-2012
摘要: We report herein a convenient route to the synthesis of aryl-substituted ?-lactones bearing an a-phosphorus ylide moiety through the assembly of dimethyl acetylenedicarboxylate (DMAD), electron-deficient aldehydes, and triaryl- or trialkylphosphanes in moderate to good yields. The formation of ?-lactones is highly dependent on the reaction time, the phosphane nucleophile, and the molar ratio of DMAD, aldehyde, and phosphane. We found that reactions with a DMAD/aldehyde/tri-p-tolylphosphane molar ratio of 3:1:6 and more electron-deficient aldehydes, such as 4-nitrobenzaldehyde and 4-chloro-3-nitrobenzaldehyde, gave good yields. The isolated ylides reacted with aldehydes as Wittig reagents to give olefins in moderate yields.
URI: http://dx.doi.org/10.1002/ejoc.201200400
http://hdl.handle.net/11536/20450
ISSN: 1434-193X
DOI: 10.1002/ejoc.201200400
期刊: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume: 
Issue: 29
起始頁: 5738
結束頁: 5747
顯示於類別:期刊論文


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