. Author manuscript; available in PMC: 2016 May 13.

Published in final edited form as: J Am Chem Soc. 2015 Apr 30;137(18):5871–5874. doi: 10.1021/jacs.5b02065

Table 2.

γ, δ–Iodolactamization of Aliphatic Amides^a,^b

Conditions: 1 (0.1 mmol), NIS (4 equiv.), TMSN₃ (4 equiv.), DCE (1 mL), 100 °C, air, 14 h.

Isolated yields.

Run on gram-scale.

Obtained as a mixture of diastereomers (See Supporting Information).

Tcp = tetrachlorophthalimide. One pot procedure for substrate 1l: NIS (2 equiv.), 100 °C, air, 8h; I₂ (3 equiv.) and TMSN₃ (4 equiv.), 100 °C, 14h.