605683-32-7

Upstream product

• 17377-95-6 benzyl(4-methoxyphenyl)amine 
• 123-38-6 propionaldehyde 
• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 147-85-3 L-proline 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 

Downstream Products

• 106-51-4 p-benzoquinone 
• 700800-36-8 (S,S)-α-methyl-β-phenylalanine 
• 837364-77-9 (2S,3R)-1-(4-methoxyphenyl)-3-methyl-2-phenylazetidine 

Relevant academic research and scientific papers

One-pot organocatalytic direct asymmetric synthesis of γ-amino alcohol derivatives

This report describes the unprecedented use of unmodified aldehydes as donors in catalytic three component one-pot asymmetric Mannich reactions. The Mannich-type reactions were also readily performed for the first time with both in situ generated and pref

PROCESS FOR THE DEPROTECTION OF PROTECTED AMINES

The present invention relates to a process for the deprotection of protected amine compounds, wherein the protected amine compound is contacted with an electrophilic oxidating agent that is optionally formed in situ, said electrophilic oxidating agent bei

Dynamic kinetic resolution in the asymmetrie synthesis of β-amino acids by organocatalytic reduction of enamines with trichlorosilane

A new methodology based on the organocatalytic asymmetric hydrosilylation of enamines that allows a direct access to a range of β3 and β2.3-amino acid derivatives was presented. The results show a successful reduction of aromatic substrates, a sterically more hindered ortho-substituted derivatives, and the thiophenyl analogue exhibiting lower reactivity. Fast enamine-imine equilibration is crucial as imines are chiral but racemic, while α-alkyl β-amino acids can be accessed by the symmetrical Mannich reaction. The α-alkyl derivatives have relative and absolute configuration due to their reduction with LiAlH4 into a known amino alcohols. Predominant formation of the anti isomer in 3o is consistent with conformation of the imine intermediate in the catalytic reduction.

PROCESS FOR THE DEPROTECTION OF PROTECTED AMINES

The present invention relates to a process for the deprotection of protected amine compounds, wherein the protected amine compound is contacted with an electrophilic oxidating agent that is optionally formed in situ, said electrophilic oxidating agent being selected from the group of I2, Br2, Cl2 and compounds comprising a halogen atom having a formal oxidation state of 1+, 3+, 5+ or 7+, provided that the electrophilic oxidating agent is not iodobenzene diacetate. The process can be conveniently employed in the synthesis of 1 ,3-amino alcohols, β-amino acids and heterocyclic compounds, in particular β-amino acids.

Enantioselective addition of aldehydes to amines via combined catalytic biomimetic oxidation and organocatalytic C-C bond formation

The biomimetic catalytic enantioselective addition of aldehydes to amines is reported. This was accomplished by combining biomimetic coupled catalytic aerobic oxidation of amines involving ruthenium-induced dehydrogenation and organocatalytic asymmetric M

The direct, enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes: The reason for the higher reactivity of aldimine versus aldehyde in proline-mediated Mannich and aldol reactions

In the proline-mediated Mannich and aldol reactions of propanal as a nucleophile, the aldimine prepared from benzaldehyde and p-anisidine is about 7 times more reactive than the corresponding aldehyde, benzaldehyde, as an electrophile. This higher reactivity of aldimine over aldehyde is attributed to the carboxylic acid of proline protonating the basic nitrogen atom of the aldimine more effectively than the oxygen atom of the aldehyde, an explanation which has been both experimentally and theoretically verified.

The Direct Catalytic Asymmetric Cross-Mannich Reaction: A Highly Enantioselective Route to 3-Amino Alcohols and α-Amino Acid Derivatives

The first proline-catalyzed direct catalytic asymmetric one-pot, three-component cross-Mannich reaction has been developed. The highly chemoselective reactions between two different unmodified aldehydes and one aromatic amine are new routes to 3-amino ald

The Direct Organocatalytic Asymmetric Mannich Reaction: Unmodified Aldehydes as Nucleophiles

The unprecedented application of unmodified aldehydes as nucleophilic donors in direct catalytic asymmetric Mannich-type reactions is disclosed in a full account. Our efforts in broadening the applicability of chiral pyrrolidine-based catalysts in direct

The direct and enantioselective, one-pot, three-component, cross-Mannich reaction of aldehydes

A double-crossed reaction: The use of proline as an organocatalyst enables a one-pot, direct, cross-Mannich reaction to be performed between two different aldehydes and 4-methoxyaniline in a highly syn-diastereo- and enantioselective manner (see scheme).