22526-49-4Relevant articles and documents
Chiral 2-imidazoline aniline compound as well as preparation method and application thereof
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Paragraph 0211-0216, (2021/07/14)
The invention provides a chiral 2-imidazoline aniline compound as well as a preparation method and application thereof. The preparation method comprises the following steps: reacting an o-nitrobenzoic acid compound as shown in a formula (1), oxalyl chloride and N, N-dimethylformamide to obtain an o-nitrobenzoyl chloride compound as shown in a formula (7); adding the hydroxyl amide derivative into a mixed solution of an amino alcohol compound as shown in a formula (2) and triethylamine to obtain a hydroxyl amide derivative as shown in a formula (3); reacting with thionyl chloride to obtain a dichloro compound as shown in a formula (4); then adding triethylamine and primary amine R2NH2 to prepare a nitroimidazoline derivative; and finally, reducing to obtain the chiral 2-imidazoline aniline compound as shown in a formula (6). The chiral 2-imidazoline aniline compound is easy to prepare, the raw materials are cheap and easy to obtain, the preparation method is simple, and the synthesized chiral ligand containing the 2-imidazoline aniline fragment can be used as a catalyst for catalyzing asymmetric hydroboration reaction of cobalt-catalyzed olefin and asymmetric hydroamination reaction of cobalt-catalyzed non-activated terminal olefin.
Enantioselective inclusion of amide guests into a chiral N,N′-ditrityl amino amide host to compensate the loss of hydrogen bonds broken by installation of trityl groups
Megumi, Ken,Yokota, Shohei,Matsumoto, Shoji,Akazome, Motohiro
supporting information, p. 707 - 710 (2013/02/23)
A new crystalline N,N′-ditrityl amino amide host included several amide guests in the host cavity to form inclusion crystals. Although the installation of trityl groups into (S)-2-aminopropanamide broke its inherent hydrogen bonds of amide groups, inclusion of guest amides compensated the loss of hydrogen bonds. X-ray crystallography showed that these inclusion cavities and host-guest interactions such as hydrogen bonds, van der Waals interaction, and CH?O interactions play important roles for highly enantioselective inclusion. The enantiomeric inclusion was 67% ee (S-form) for N-phenyl 2-methylbutanamide, 82% ee (S-form) for N-phenyl 2-chlorobutanamide, and 83% ee (S-form) for N-phenyl 2-bromobutanamide.
Stereoselective Synthesis of Enantiopure Amino Compounds, via Mitsunobu Azidation of (2S,Rs)-1-(p-Tolylsulfinyl)butan-2-ol
Bravo, Pierfrancesco,Cavicchio, Giancarlo,Crucianelli, Marcello,Poggiali, Andrea,Volonterio, Alessandro,Zanda, Matteo
, p. 666 - 667 (2007/10/03)
Azidation of (2S,Rs)-1-(p-tolysulfinyl)butan-2-ol under Mitsunobu conditions is the key step for a highly stereoselective preparation of enantiomerically pure amino compounds via chiral sulfoxide chemistry.
