75475-77-3

Upstream product

• 75475-78-4 O-benzyloxycarbonyl-N-(S)-(1-phenylethyl)-(S)-mandelamide 
• 10549-16-3 N-<(S)-α-methylbenzyl>benzoylformamide 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 17199-29-0 (S)-Mandelic acid 
• 2627-86-3 (-)-α-methylbenzylamine 
• 90-64-2 (+)-mandelic acid 
• 17329-20-3 (S)-1-isocyano-1-phenylethane 
• 100-52-7 benzaldehyde 
• 110901-05-8 O-benzyloxycarbonyl-(S)-(+)-mandelic acid 
• 4358-87-6 (RS)-methyl mandelate 
• 21210-43-5 (S)-Methyl mandelate 

Downstream Products

• 91578-85-7 (S)-1-phenyl-2-((1S)-1-phenylethylamino)ethan-1-ol 

Relevant academic research and scientific papers

N-(S)-(1-phenethyl)-(S)-mandelic amide, and synthesis method, intermediate and medicine thereof

The invention belongs to the field of organic synthesis, and particularly relates to N-(S)-(1-phenethyl)-(S)-mandelic amide, and a synthesis method, an intermediate and a medicine thereof. The synthesis method of the N-(S)-(1-phenethyl)-(S)-mandelic amide

Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides

An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.

Catalytic asymmetric transfer hydrogenation of ketones using [Ru(p-cymene)Cl2]2 with chiral amino alcohol ligands

Catalytic asymmetric transfer hydrogenation of aromatic alkyl ketones has been investigated using [Ru(p-cymene)Cl2]2 and new derivatives of β-amino alcohols synthesized from (S)-(-)-lactic acid and mandelic acid as ligands. Chiral secondary alcohols were obtained with good to excellent conversion (60-90%) and moderate to good enantioselectivities (40-86%).

Enantioselective addition of dimethylzinc to aldehydes catalyzed by N-substituted mandelamide-Ti(IV) complexes

Amides derived from (S)-(+)-mandelic acid in the presence of titanium isopropoxide catalyze the enantioselective addition of dimethylzinc to aromatic aldehydes with good yields and ee up to 90%.

Catalytic, enantioselective α-additions of isocyanides: Lewis base catalyzed Passerini-type reactions

The generality of catalytic, enantioselective α-additions of isocyanides to aldehydes has been demonstrated (Passerini-type reactions). The catalytic system of silicon tetrachloride and a chiral bisphosphoramide (R,R)-1b provided high yields and good to excellent enantioselectivities for the addition of tert-butyl isocyanide to a wide range of aldehydes (aromatic, heteroaromatic, olefinic, acetylenic, aliphatic). Aqueous workup afforded the α-hydroxy tert-butyl amides whereas a low-temperature methanol quench followed by basic workup afforded the α-hydroxy methyl esters. The reaction is also successful for other isocyanides, albeit with reduced enantioselectivity. Reaction conditions, particularly the rate of addition of the isocyanide was found to be crucial for good yields and high selectivities.

Resolution of (±)-mandelic- and (±)-2-(chiorophenoxy)propionic-acid derivatives by crystallization of their diastereomeric amides with (R)- or (S)-α-arylethylamines

An alternative and cost effective route for the resolution in high ees (95-99%) of (±)-mandelic-and (±)-2-(chlorophenoxy)propionic- acid derivatives is reported. The key step involves the covalent derivatization and separation of their diastereomeric amides with (R)- or (S)-α- arylethylamines.

Resolution of (±)-mandelic- and (±)-2-(chlorophenoxy)propionic-acid derivatives by crystallization of their diastereomeric amides with (R)- or (S)-α-arylethylamines

An alternative and cost effective route for the resolution in high ees (95-99%) of (±)-mandelic-and (±)-2-(chlorophenoxy)propionic- acid derivatives is reported. The key step involves the covalent derivatization and separation of their diastereomeric amides with (R)- or (S)-α- arylethylamines.

The Preparation and Absolute Configuration of the Optically Active Forms of the Diastereoisomers of 2-(1-Phenylethyl)amino-1-phenylethanol and Their Use as Chiral Auxiliaries in the Asymmetric Reduction of Acetophenone with Modified Lithium Aluminium Hydrides

(1S,2S)-(-)-2-(1-Phenylethyl)amino-1-phenylethanol (4b) (α-form) and the (1S,2R)-(+)-diastereoisomer (4f) (β-form) were prepared by lithium aluminium hydride reduction of the optically active amides derived from the appropriate mandelic acids and 1-phenylethylamines.The preparative methods give the absolute stereochemistry.The aminoethanols (4) were used along with the lower alcohols to prepare chirally modified lithium aluminium hydrides which were in turn used to reduce acetophenone.The optical yields varied, giving at best, under low temperature conditions and use of a 25 percent optical yield.

ASYMMETRIC CATALYTIC HYDROGENATIONS OF CHIRAL alpha -KETO AMIDES.

Asymmetric catalytic hydrogenations of chiral pyruvamides were carried out using palladium on charcoal (Pd-C) as a catalyst to give lactamides with the diastereoisomeric purities (d. p. ) of up to 62%. It was found that there was a linear correlation betw