Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
Institute of Inorganic and Analytical Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392 Giessen, Germany.
Org Biomol Chem. 2021 May 12;19(18):4027-4031. doi: 10.1039/d1ob00471a.
We describe a triflic acid promoted cascade reaction of adamantane derivatives consisting of a decarboxylation of N-methyl protected cyclic carbamates and a subsequent intramolecular nucleophilic 1,2-alkyl shift to generate ring contracted iminium triflates. This reaction expands the family of similar transformations, such as Wagner-Meerwein-, Demjanov-Tiffeneau-, Meinwald- or (semi-)pinacol-rearrangement. It allows the preparation of noradamantane derivatives in a few steps, starting from simple hydroxy-substituted adamantane precursors.
我们描述了三氟乙酸促进的金刚烷衍生物的级联反应，包括 N-甲基保护的环状氨基甲酸酯的脱羧反应和随后的分子内亲核 1,2-烷基迁移，生成环收缩的亚胺三氟甲磺酸酯。该反应扩展了类似的转化家族，如 Wagner-Meerwein-、Demjanov-Tiffeneau-、Meinwald- 或（半）频哪醇重排。它允许从简单的羟基取代的金刚烷前体出发，通过几步反应制备降金刚烷衍生物。
