916685-60-4Relevant academic research and scientific papers
AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS
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Paragraph 0008-0009; 0063-0064, (2022/03/04)
The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.
Amine-boranes as Dual-Purpose Reagents for Direct Amidation of Carboxylic Acids
Choudhary, Shivani,Hamann, Henry J.,Ramachandran, P. Veeraraghavan
, (2020/11/13)
Amine-boranes serve as dual-purpose reagents for direct amidation, activating aliphatic and aromatic carboxylic acids and, subsequently, delivering amines to provide the corresponding amides in up to 99% yields. Delivery of gaseous or low-boiling amines as their borane complexes provides a major advantage over existing methodologies. Utilizing amine-boranes containing borane incompatible functionalities allows for the preparation of functionalized amides. An intermolecular mechanism proceeding through a triacyloxyborane-amine complex is proposed.
Enzyme-like chemoselective acylation of alcohols in the presence of amines catalyzed by a tetranuclear zinc cluster
Ohshima, Takashi,Iwasaki, Takanori,Maegawa, Yusuke,Yoshiyama, Asako,Mashima, Kazushi
, p. 2944 - 2945 (2008/09/20)
Acylation of alcohols and amines is one of the most fundamental reactions. Due to the greater nucleophilicity of the amino group compared to the hydroxyl group, complete N-acylation occurs. Only an enzymatic reaction can promote a highly selective O-acyla
Kinetic resolution of vic-amino alcohols catalyzed by a chiral Cu(II) complex
Mitsuda, Masaru,Tanaka, Tomoaki,Tanaka, Toshimitsu,Demizu, Yosuke,Onomura, Osamu,Matsumura, Yoshihiro
, p. 8073 - 8077 (2007/10/03)
Kinetic resolution of N-benzoylated vic-amino alcohols was achieved by benzoylation in the presence of copper triflate and (R,R)-Ph-BOX as catalysts. The observed enantioselectivity was moderate to high. The method was applied to a kinetic resolution of r
