Highly Chemoselective Aerobic Oxidation of Amino Alcohols into Amino Carbonyl Compounds |
| |
Authors: | Yusuke Sasano Shota Nagasawa Mai Yamazaki Dr. Masatoshi Shibuya Prof. Dr. Jaiwook Park Prof. Dr. Yoshiharu Iwabuchi |
| |
Affiliation: | 1. Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, 6‐3 Aoba, Aramaki, Aoba‐ku, Sendai 980‐8578 (Japan);2. Current address: Department of Basic Medicinal Sciences, Graduate School of Pharmaceutical Sciences, Nagoya University, Furo‐cho, Chikusa‐ku, Nagoya 464‐8601 (Japan);3. Department of Chemistry, POSTECH (Pohang University of Science and Technology), Pohang 790‐784 (Republic of Korea) |
| |
Abstract: | 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. |
| |
Keywords: | amino alcohol chemoselectivity copper oxidation radical chemistry |
|
|