An alkoxide anion-triggered tert-butyloxycarbonyl group migration. Mechanism and application

作者：Xue Fengtian; Silverman Richard B^*

来源：Tetrahedron Letters, 2010, 51(18): 2536-2538.

DOI：10.1016/j.tetlet.2010.03.009

• N to O migration
• Boc group migration
• Intramolecular migration
• Cross-over experiment

We report a fast N -> O tert-butyloxycarbonyl (Boc) migration of the imide (3R,4R)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-hydroxypyrrolidine-1-carboxylate (2) via a base-generated alkoxide. The mechanism of the migration is intramolecular, involving an unusual nine-membered cyclic transition state.

• 出版日期2010-5-5
• 单位西北大学