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In a typical general procedure, 1.1 equiv of the appropriate 3-indoleacetic acid was dissolved in CH2Cl2 and 4.0 equiv of oxalyl chloride was added dropwise. The solution was stirred overnight and then concentrated under reduced pressure. The resulting solid was taken up in THF, which was immediately added to a vigorously stirred mixture containing 1.0 equiv of the diazo lactam (i.e. 19 or 20) and 4 Å MS in THF. After stirring for 12 h, the mixture was filtered through a pad of Celite® and concentrated under reduced pressure. The crude material was purified by flash silica gel column chromatography to give the desired coupled product. Using this procedure, 3-{3-(2-benzyloxyethyl)-1-[2-(1-methyl-1H-indol-3- yl)acetyl]-2-oxopiperidin-3-yl}-2-diazo-3-oxopropionic acid methyl ester (16d) was obtained as a colorless oil in 82% yield. IR (neat, 2143, 1718, 1685, 1332, 1146 cm-1. 1H NMR 400 MHz, CDCl 3
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2 was added 2 mg rhodium(II) acetate, and the mixture was heated at reflux for 1 h. The mixture was allowed to cool to r.t. and was filtered through a pad of Celite®. The solvent was removed under reduced pressure and the residue was subjected to flash silica gel chromatography to give 0.16 g (96%) of the dipolar- cycloaddition product 21d.
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