Highly Chemoselective Aerobic Oxidation of Amino Alcohols into Amino Carbonyl Compounds
Highly Chemoselective Aerobic Oxidation of Amino Alcohols into Amino Carbonyl Compounds
复制标题
DOI：
10.1002/anie.201309634
复制
发表时间：
2014-03-17
影响因子：
16.6
通讯作者：
Iwabuchi, Yoshiharu
中科院分区：
文献类型：
--
作者：
Sasano, Yusuke;Nagasawa, Shota;Iwabuchi, Yoshiharu
将未保护的氨基醇直接氧化成其相应的氨基羰基化合物常常在有机合成中提出严重的挑战，并且限制化学家采用间接途径，例如保护/脱保护策略，以实现其目标。本文描述了一种未保护的氨基醇高化学选择性需氧氧化成其氨基羰基化合物的方法，其中使用2-氮杂金刚烷N-氧基（AZADO）/铜催化。开发的催化系统导致各种未保护的氨基醇的醇选择性氧化，携带伯，仲，或叔氨基，在环境温度下暴露于空气中的良好到高产率，从而提供了灵活的含氮化合物的合成。
The direct oxidation of unprotected amino alcohols to their corresponding amino carbonyl compounds has often posed serious challenges in organic synthesis and has constrained chemists to adopting an indirect route, such as a protection/deprotection strategy, to attain their goal. Described herein is a highly chemoselective aerobic oxidation of unprotected amino alcohols to their amino carbonyl compounds in which 2-azaadamantane N-oxyl (AZADO)/copper catalysis is used. The catalytic system developed leads to the alcohol-selective oxidation of various unprotected amino alcohols, carrying a primary, secondary, or tertiary amino group, in good to high yield at ambient temperature with exposure to air, thus offering flexibility in the synthesis of nitrogen-containing compounds.