49681-46-1

Upstream product

• 2936-62-1 (RS)-(2-methylphenyl)phenylmethylamine 
• 22627-00-5 2-methyl-benzophenone-imine 
• 529-20-4 2-methylphenyl aldehyde 
• 1309582-46-4 N,N'-bis[(2-methylphenyl)methylidene]sulfamide 
• 1309582-61-3 N,N'-sulfonyl bis-[(S)-(2-methylphenyl)(phenyl)methylamine] 

Downstream Products

• 1351866-42-6 (S)-(+)-N-[(2-methylphenyl)(phenyl)methyl]acetamide 

Relevant academic research and scientific papers

Highly Stereoselective Strecker Synthesis Induced by a Slight Modification of Benzhydrylamine from Achiral to Chiral

2-Methylbenzhydrylamine is a chiral variant of achiral benzhydrylamine; however, the chirality formed from the small difference between the phenyl and o-tolyl groups is not expected to induce sufficient stereoselectivity in conventional homogeneous reactions. Initiated by the spontaneous formation and asymmetric amplification of the enantioenriched N-benzhydryl-α-aminonitrile forming conglomerate, we here report that (S)- and (R)-configured title amine, upon the Strecker reaction with achiral aldehydes and HCN, afford the corresponding α-aminonitriles with up to >99.5 % diastereomeric excess, in conjunction with an enhancement of chirality in the solid state. l-Alanine with 98 % ee was synthesized from the (S)-amine by using the method discussed here. Achiral aromatic and heteroaromatic aldehydes could also be successfully utilized to afford chiral α-aminonitriles in a highly stereoselective manner. The stereodivergent synthesis of styrylglycine nitriles has also been accomplished by using racemic and enantioenriched 2-methylbenzhydrylamine. Thus, accompanied with a small rearrangement of the common substrate from achiral toward chiral, the present reactions induce an enhancement of chirality, and expands the concept of stereoselective synthesis to increase the opportunity to access highly enantioenriched compounds such as α-amino acids.

MANUFACTURING METHOD OF OPTICALLY ACTIVE AMINONITRILE COMPOUND AND MANUFACTURING METHOD OF OPTICALLY ACTIVE AMINO ACID

PROBLEM TO BE SOLVED: To provide a method for manufacturing an optically active aminonitrile compound with high purity suitable for manufacturing optically active amino acid and a method for manufacturing an optically active amino acid. SOLUTION: An optically active imine compound is obtained by condensing an optically active primary amine compound and a carbonyl compound in a solvent, a crystal of an optically active aminonitrile compound is deposited by adding hydrogen cyanide or a salt thereof to the imine compound in a solvent and asymmetric amplification for extremely enhancing diastereomer ratio thereof is conducted. The resulting aminonitrile compound with high optical purity is converted to optically active amino acid by known acid hydrolysis without deteriorating optical purity. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2017,JPOandINPIT

Enantioselective Hydrogenation of Diarylmethanimines for Synthesis of Chiral Diarylmethylamines

An enantioselective hydrogenation of N-substituted diarylmethanimines under mild conditions has been first realized by using an iridium catalyst with a chiral f-spiroPhos ligand. This method provides an efficient access to the asymmetric synthesis of a variety of chiral diarylmethylamines and their derivatives with excellent enantioselectivities (up to 99.4% ee) and high turnover numbers (TON up to 4000).

Bis-sulfamyl imines: Potent substrates for asymmetric additions of arylboroxines under rhodium catalysis

Bis-sulfamyl imines are shown to be potentially ideal substrates for rhodium-catalysed asymmetric additions of arylboron nucleophiles as they show: (i) near perfect enantioselectivities (11 examples, 98-99+% ee), (ii) good to excellent diastereoselectivities (10-32:1 rac:meso), and (iii) high functional group tolerance in removal of the low molecular weight protecting group via mild heating in aqueous pyridine.