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Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYL-1-BUTANOL is used as a chiral building block for the synthesis of various pharmaceutical compounds. Its unique structure and stereochemistry make it a valuable intermediate in the development of enantiomerically pure drugs, which can exhibit improved efficacy and reduced side effects compared to their racemic counterparts.
Used in Organic Synthesis:
(S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYL-1-BUTANOL is used as a versatile intermediate in organic synthesis for the preparation of a wide range of organic compounds, including amino alcohols, chiral ligands, and catalysts. Its reactivity and functional groups allow for various chemical transformations, making it a useful component in the synthesis of complex organic molecules.
Used in Chiral Pool Synthesis:
(S)-(-)-2-AMINO-3-METHYL-1,1-DIPHENYL-1-BUTANOL is used as a chiral source in chiral pool synthesis, a strategy that involves the use of chiral compounds as starting materials to synthesize enantiomerically pure target molecules. Its unique stereochemistry and functional groups make it a valuable building block for the preparation of chiral compounds with potential applications in various industries, such as pharmaceuticals, agrochemicals, and fragrances.

InChI:InChI=1/C17H21NO/c1-13(2)16(18)17(19,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-13,16,19H,18H2,1-2H3/t16-/m0/s1

Upstream product

• 7146-15-8 D-Valine methyl ester hydrochloride 
• 6306-52-1 L-valine methylester hydrochloride 
• 100-39-0 benzyl bromide 
• 100-58-3 phenylmagnesium bromide 
• 4070-48-8 L-Valine methyl ester 
• 108-86-1 bromobenzene 
• 17609-47-1 L-Valine ethyl ester hydrochloride 
• 72-18-4 L-valine 
• 130432-39-2 (S)-1-hydroxy-3-methyl-1,1-diphenylbutan-2-aminium chloride 
• 57728-40-2 (-)-2-amino-3-methyl-1,1-diphenylbutanol 
• 100-59-4 phenylmagnesium chloride 
• 501-53-1 benzyl chloroformate 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 24210-19-3 methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate 

Downstream Products

• 184346-45-0 (S)-5,5-Diphenyl-4-isopropyl-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Simple primary β-amino alcohols as organocatalysts for the asymmetric Michael addition of β-keto esters to nitroalkenes

Simple primary β-amino alcohols act as an efficient organocatalysts in the asymmetric Michael addition of β-keto esters with nitroalkenes affording highly pure chiral Michael adducts. Also, both enantiomers of the adducts were obtained, depending on the specific catalyst used and reaction temperature.

The Asymmetric Aza-silyl-Prins Reaction: Synthesis of Enantiopure Piperidines

The design and development of the first asymmetric aza-silyl-Prins reaction is reported, giving rise to valuable and diverse piperidines and pipecolic acid derivatives in both high yields and as single enantiomers. The creation of a novel chiral auxiliary-homoallylic amine for the aza-silyl-Prins reaction is essential to its success.

Catalytic intramolecular hydroamination of aminoallenes using titanium complexes of chiral, tridentate, dianionic imine-diol ligands

Alkylation of d- or l-phenylalanine or valine alkyl esters was carried out using methyl or phenyl Grignard reagents. Subsequent condensation with salicylaldehyde, 3,5-di-tert-butylsalicylaldehyde, or 5-fluorosalicylaldehyde formed tridentate, X2/sub

Hybrid-Type Squaramide-Fused Amino Alcohol Organocatalysts for Enantioselective Nitro-Aldol Reaction of Nitromethane with Isatins

A series of hybrid-type squaramide-fused amino alcohol (SFAA) catalysts were synthesized, and their catalytic efficiency in the enantioselective nitro-aldol reaction of various isatins with nitromethane has been described. This transformation afforded chiral 3-substituted 3-hydroxyoxindoles in excellent chemical yields (up to 99 %) with high enantioselectivities (up to 95 % ee). The resulting chiral 3-hydroxyoxindoles can be further used as synthetic precursors for the synthesis of several natural products that have a broad spectrum of fascinating biological activities.

NeoPHOX - A structurally tunable ligand system for asymmetric catalysis

A synthesis of new NeoPHOX ligands derived from serine or threonine has been developed. The central intermediate is a NeoPHOX derivative bearing a methoxycarbonyl group at the stereogenic center next to the oxazoline N atom. The addition of methylmagnesiu

Simple primary β-amino alcohol catalyzed enantioselective Diels-Alder reaction of 3-hydroxy-2-pyridones

The simple primary β-amino alcohol catalyzed Diels-Alder reaction of 3-hydroxy-2-pyridones as dienes with N-substituted maleimides to provide the highly substituted optically active isoquinuclidines as a single diastereomers in excellent enantioselectivities (up to 98%) with excellent chemical yields (up to 95%) was demonstrated. A range of simple β-amino alcohols were synthesized from the corresponding inexpensive amino acids and their catalytic activity was examined for this reaction.

Bisoxazolidine ligand and a catalyst using the same (by machine translation)

PROBLEM TO BE SOLVED: To establish a manufacturing method of a bisoxazolidine ligand and a catalytic reaction using the same.SOLUTION: There is provided a bisoxazolidine ligand represented by the formula (1) or (2). (1) (2), where Ris any of CH3, CH(CH3)2

A method for producing an optically active Alkylaminosulfonamide deriv. β-amino alcohol derivative and optically active

PROBLEM TO BE SOLVED: To provide a method for producing an optically active alkylaminosulfonamide derivative useful in pharmaceutical applications etc., and an optically active β-aminoalcohol derivative. SOLUTION: The optically active alkylaminosulf

Synthesis and applications in Henry reactions of novel chiral thiazoline tridentate ligands

Several novel chiral tridentate ligands containing thiazoline were efficiently synthesized from commercially available l=cysteine in high yield. These ligands were subsequently applied to the asymmetric Henry reaction of nitromethane and various aldehydes. It was found that the structures of the thiazoline ligands had a significant influence on the enantioselectivity. It was shown that the optimal catalyst for this reaction was a ligand complexed with CuCl, which was formed from chiral thiazoline with chiral aminoalcohol. At -20°C, with 10 mol% of this ligand, a product with (S)-configuration was isolated in 93% yield and 98% enantiomeric excess.

Silyloxy Amino Alcohol Organocatalyst for Enantioselective 1,3-Dipolar Cycloaddition of Nitrones to α,β-Unsaturated Aldehydes

The catalytic activity of a simple amino alcohol that contains a bulky super silyl group [i.e., tris(trimethylsilyl)silyl (TTMSS)] bonded to the oxygen atom at the γ-position along with a primary amine moiety was examined in the enantioselective 1,3-dipolar cycloaddition of nitrones to α,β-unsaturated aldehydes. The organocatalyst successfully provided optically active isoxazolidines in good chemical yields (up to 86 %) with excellent diastereoselectivities (endo/exo, up to 96:4) and enantioselectivities (up to 97 % ee). Furthermore, the obtained isoxazolidines were easily converted into γ-amino diols that contain three contiguous stereogenic centers.