alpha-Triethylsilyl-alpha-diazoacetone in double cross-aldolisation: convenient acetone equivalent toward 5-hydroxy-1,3-diketones

作者：Lancou Anthony; Haroun Heloua; Kundu Uday K; Legros Frederic; Zimmermann Nicolas; Mathe Allainmat Monique; Lebreton Jacques; Dujardin Gilles; Gaulon Nourry Catherine; Gosselin Pascal^*

来源：Tetrahedron, 2012, 68(47): 9652-9657.

DOI：10.1016/j.tet.2012.09.063

• Diazoacetone
• Silyl-protected diazoacetone
• Aldolisation
• Dediazotation
• Rhodium acetate

alpha-Triethylsilyl-alpha-diazoacetone underwent a sequential aldolisation-deprotection-aldolisation process to access the 2-diazo-3-oxo-1,5-dihydroxy skeleton with significant diversity. The diazo group could be efficiently removed by treatment with rhodium acetate to afford the corresponding 5-hydroxy-1,3-diketones.

• 出版日期2012-11-25