92520-13-3Relevant articles and documents
Biocatalytic, Intermolecular C?H Bond Functionalization for the Synthesis of Enantioenriched Amides
Arnold, Frances H.,Athavale, Soumitra V.,Gao, Shilong,Hirschi, Jennifer S.,Liu, Zhen,Mallojjala, Sharath Chandra
supporting information, p. 24864 - 24869 (2021/10/15)
Directed evolution of heme proteins has opened access to new-to-nature enzymatic activity that can be harnessed to tackle synthetic challenges. Among these, reactions resulting from active site iron-nitrenoid intermediates present a powerful strategy to forge C?N bonds with high site- and stereoselectivity. Here we report a biocatalytic, intermolecular benzylic C?H amidation reaction operating at mild and scalable conditions. With hydroxamate esters as nitrene precursors, feedstock aromatic compounds can be converted to chiral amides with excellent enantioselectivity (up to >99 % ee) and high yields (up to 87 %). Kinetic and computational analysis of the enzymatic reaction reveals rate-determining nitrenoid formation followed by stepwise hydrogen atom transfer-mediated C?H functionalization.
Chemoselective formation of C–N bond in wet acetonitrile using amberlyst-15(H) as a recyclable catalyst
Nandy, Sneha,Das, Asit Kumar,Bhar, Sanjay
supporting information, p. 3326 - 3336 (2020/08/13)
An economically efficient and environmentally benign protocol for the chemoselective one-pot synthesis of diversely N-substituted amides has been developed in good yield through the reaction of benzylic secondary alcohols as well as aliphatic tertiary alcohols and alkyl/aryl nitriles. Commercially available Amberlyst-15(H) has been utilized at 80 °C as an air-stable and reusable heterogeneous inexpensive solid acid catalyst without any anhydrous and inert environment. The attractive features of the present synthetic protocol are mild reaction conditions, short reaction time, excellent chemoselectivity, high atom economy and tolerance of various sensitive moieties.
A Single Lipase-Catalysed One-Pot Protocol Combining Aminolysis Resolution and Aza-Michael Addition: An Easy and Efficient Way to Synthesise β-Amino Acid Esters
Xu, Fan,Wu, Qiongsi,Chen, Xiaoyang,Lin, Xianfu,Wu, Qi
, p. 5393 - 5401 (2015/08/24)
A novel one-pot protocol combining aza-Michael addition and aminolysis resolution was developed to obtain chiral β-amino acid esters with lipase B from Candida antarctica (CAL-B) as the only catalyst. This method is conducted under mild reaction conditions and is very easy to handle. After a series of detailed optimization studies, ten racemic aromatic or aliphatic amines were subjected to this one-pot procedure, and twelve chiral β-amino acid esters and ten chiral amides were successfully synthesised with excellent ee values in theoretical yields. Scaled-up procedures also worked without apparent reduction in reaction rate or enantioselectivity, which makes this method suitable for large-scale production of chiral β-amino acid esters. A one-pot protocol for simultaneous synthesis of chiral β-amino acid esters and amides was developed by combining single lipase B from Candida antarctica (CAL-B) catalysed aza-Michael addition and aminolysis resolution. This method requires mild reaction conditions and is very easy to handle. Chiral β-amino acid esters and chiral amides were obtained with excellent ee values and in theoretical yields.
