Zhou, Zijun; Tan, Yuqi; Shen, Xiang; Ivlev, Sergei; Meggers, Eric published an article in 2021. The article was titled 《Catalytic enantioselective synthesis of β-amino alcohols by nitrene insertion》, and you may find the article in Science China: Chemistry.Electric Literature of C9H11NO The information in the text is summarized as follows:
Herein, a general intramol. C(sp3)-H nitrene insertion method for the synthesis of chiral oxazolidin-2-ones as precursors of chiral β-amino alcs was reported. Specifically, the ring-closing C(sp3)-H amination of N-benzoyloxycarbamates with 2 mol% of a chiral ruthenium catalyst provides cyclic carbamates in up to 99% yield and with up to 99% ee. The method was applicable to benzylic, allylic, and propargylic C-H bonds and can even be applied to completely non-activated C (sp3)-H bonds, although with somewhat reduced yields and stereoselectivities. The obtained cyclic carbamates was subsequently be hydrolyzed to obtain chiral β-amino alcs. The method was very practical as the catalyst was easily synthesized on a gram scale and was recycled after the reaction for further use. The synthetic value of the new method was demonstrated with the asym. synthesis of a chiral oxazolidin-2-one as intermediate for the synthesis of the natural product aurantioclavine and chiral β-amino alcs. that are intermediates for the synthesis of chiral amino acids, indane-derived chiral Box-ligands, and the natural products dihydrohamacanthin A and dragmacidin A. The results came from multiple reactions, including the reaction of (1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7Electric Literature of C9H11NO)
(1S,2R)-1-Amino-2,3-dihydro-1H-inden-2-ol(cas: 126456-43-7) belongs to anime. Milder oxidation, using reagents such as NaOCl, can remove four hydrogen atoms from primary amines of the type RCH2NH2 to form nitriles (R―C≡N), and oxidation with reagents such as MnO2 can remove two hydrogen atoms from secondary amines (R2CH―NHR′) to form imines (R2C=NR′). Tertiary amines can be oxidized to enamines (R2C=CHNR2) by a variety of reagents.Electric Literature of C9H11NO
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts