22526-49-4

Upstream product

• 61448-31-5 (S)-(-)-N-(1-Methyl-2-propinyl)-benzamid 
• 513-49-5 (S)-2-aminobutane 
• 98-88-4 benzoyl chloride 
• 33966-50-6 SEC-BUTYLAMINE 
• 106-98-9 1-butylene 
• 952524-02-6 (S)-1-benzoyl-2-(α-acetoxyethyl)benzimidazole 
• 219141-87-4 N-[(R)-1-((R)-Toluene-4-sulfinylmethyl)-propyl]-benzamide 
• 219141-88-5 N-(1-p-tolylsulfanylmethyl-propyl)-benzamide 
• 159717-44-9 (R)-N-(1-chloromethylpropyl)benzamide 

Downstream Products

• 100-47-0 benzonitrile 

Relevant academic research and scientific papers

Chiral 2-imidazoline aniline compound as well as preparation method and application thereof

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.

Ruthenium Catalyzed Direct Asymmetric Reductive Amination of Simple Aliphatic Ketones Using Ammonium Iodide and Hydrogen

The direct conversion of ketones into chiral primary amines is a key transformation in chemistry. Here, we present a ruthenium catalyzed asymmetric reductive amination (ARA) of purely aliphatic ketones with good yields and moderate enantioselectivity: up to 99 percent yield and 74 percent ee. The strategy involves [Ru(PPh3)3H(CO)Cl] in combination with the ligand (S,S)-f-binaphane as the catalyst, NH4I as the amine source and H2 as the reductant. This is a straightforward and user-friendly process to access industrially relevant chiral aliphatic primary amines. Although the enantioselectivity with this approach is only moderate, to the extent of our knowledge, the maximum ee of 74 percent achieved with this system is the highest reported till now apart from enzyme catalysis for the direct transformation of ketones into chiral aliphatic primary amines.

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

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.

Enantioselective benzoylation of racemic amines using chiral benzimidazolide as a benzoylating agent

Enantioselective acylation/kinetic resolution of racemic amines has been achieved by using a chiral benzimidazolide, namely, (S)-1-benzoyl-2-(α-acetoxyethyl)benzimidazole 2. This nonenzymatic acylating reagent requires mild reaction conditions and proceeds with good enantioselectivity.

Stereoselective Synthesis of Enantiopure Amino Compounds, via Mitsunobu Azidation of (2S,Rs)-1-(p-Tolylsulfinyl)butan-2-ol

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.

EPC-synthesis of functionalised amides via chiral β-nitrogenated organolithium compounds

The deprotonation of chiral chloroamides or carbamates 1, 4, 7, 10, 13 and 16 with n-butyllithium followed by in situ lithiation with lithium naphthalenide, both at -78°C in THF, leads to the formation of the corresponding chiral dianionic intermediates,

Synthesis of enantiomerically pure functionalised amides (EPC-synthesis) from chiral β-aminated organolithium intermediates

The successive deprotonation-lithiation of chiral chloroamides 1 with n-butyllithium and lithium naphthalenide, respectively, at -78°C leads to the corresponding chiral β-aminated organolithium intermediates 2, which by reaction with different electrophil

Synthesis of (R)- and (S)-2-Aminobutane from (S)- and (R)-2-Aminobutanol

(R)-(-)- and (S)-(+)-2-Aminobutane (1) can be synthesized in good yield and high optical purity from (S)-(+)- and (R)-(-)-2-aminobutanol (2) respectively.