Tandem cyclization-cycloaddition reaction of rhodium carbenoids. Studies dealing with the geometric requirements of dipole formation

A Padwa, RL Chinn, SF Hornbuckle…

文献索引：Padwa, Albert; Chinn, Richard L.; Hornbuckle, Susan F.; Zhang, Zhijia J. Journal of Organic Chemistry, 1991 , vol. 56, # 10 p. 3271 - 3278

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被引用次数: 78

摘要

7 the rhodium (I1) catalyst at 25 OC in methylene chloride afforded 5-ethoxy-4-methyl-3-(2H)- furanone (6) in 90% isolated yield. We believe that the mechanism by which 4 is converted into 6 involves rapid cyclization of the rhodium carbenoid onto the neighboring carbonyl group to give the five-ring carbonyl ylide 5, which undergoes a subsequent proton transfer. le All attempts to trap the suspected 1, 3-dipole with a variety of dipolarophiles failed to ...