219500-45-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(-)-(S)-2-bromo-3-phenylpropan-1-ol is used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. Its unique structure and properties make it a valuable component in the development of new drugs.
Used in Antimicrobial and Antifungal Applications:
(-)-(S)-2-bromo-3-phenylpropan-1-ol has been studied for its antimicrobial and antifungal properties, indicating its potential use in the development of new drugs to combat infections and fungal growth.
Used as a Chiral Resolving Agent:
(-)-(S)-2-bromo-3-phenylpropan-1-ol is utilized as a chiral resolving agent, which is essential in the separation of enantiomers, a critical process in the production of pure pharmaceutical compounds.
Used in Synthesis of Chiral Ligands:
Additionally, it serves as a precursor in the synthesis of chiral ligands for asymmetric syntheses, a key technique in creating enantiomerically pure compounds, which is particularly important in the pharmaceutical industry where the desired biological activity often resides in just one enantiomer.

Upstream product

• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 51075-28-6 2-bromo-3-phenylpropanal 
• 104-54-1 3-Phenylpropenol 
• 1450891-89-0 (+)-(2R,3S)-2-bromo-3-chloro-3-phenylpropan-1-ol 
• 124916-61-6 (S)-2-bromo-3-penylpropanoic acid methyl ester 
• 35016-63-8 (S)-2-bromo-3-phenylpropionic acid 
• 63-91-2 L-phenylalanine 

Downstream Products

• 947687-18-5 (R)-2-benzylmorpholine 
• 1517-68-6 (S)-1-phenylpropan-2-ol 
• 61393-94-0 (R)-2-benzyloxirane 

Relevant academic research and scientific papers

Development of Ketone-Based Brominating Agents (KBA) for the Practical Asymmetric α-Bromination of Aldehydes Catalyzed by Tritylpyrrolidine

Ketone-based brominating agents (KBA), ortho-substituted 2,2,2-tribromoacetophenones, have been developed, and the highly enantioselective and practical α-bromination of aldehydes with KBA was achieved. The reaction could be performed in the presence of only 0.1-1 mol % of catalyst without using a halogenated solvent at 0 °C and was found to be scalable.

Enantiospecific Solvolytic Functionalization of Bromochlorides

Herein, we report that under mild solvolytic conditions, enantioenriched bromochlorides can be ionized, stereospecifically cyclized to an array of complex bromocyclic scaffolds, or intermolecularly trapped by exogenous nucleophiles. Mechanistic investigations support an ionic mechanism wherein the bromochloride serves as an enantioenriched bromonium surrogate. Several natural product-relevant motifs are accessed in enantioenriched form for the first time with high levels of stereocontrol, and this technology is applied to the scalable synthesis of a polycyclic brominated natural product. Arrays of nucleophiles including olefins, alkynes, heterocycles, and epoxides are competent traps in the bromonium-induced cyclizations, leading to the formation of enantioenriched mono-, bi-, and tricyclic products. This strategy is further amenable to intermolecular coupling between cinnamyl bromochlorides and a diverse set of commercially available nucleophiles. Collectively, this work demonstrates that enantioenriched bromonium chlorides are configurationally stable under solvolytic conditions in the presence of a variety of functional groups.

α-amination of aldehydes catalyzed by in situ generated hypoiodite

The metal-free amination of different aldehydes is catalyzed by hypoiodite, which is generated by employing commercially available sodium percarbonate as the co-oxidant. This approach has several advantages: it is a metal-free oxidation that works under m

Direct asymmetric bromination of aldehydes catalyzed by a binaphthyl-based secondary amine: Highly enantio- and diastereoselective one-pot synthesis of bromohydrins

One-pot stereoselective synthesis of bromohydrins as a useful chiral building block was achieved by the reaction of Grignard reagents with optically active α-bromoaldehydes, which were in situ generated by direct asymmetric bromination of aldehydes cataly

Extractive biocatalysis: A powerful tool in selectivity control in yeast biotransformations

The effect of absorbing resins on the yeast reduction of α,β- unsaturated carbonyl compounds is reported. Enantioselectivity, chemoselectivity and space-time yields of the biotransformation are impressively enhanced. The distribution of substrates and products between the resin and the water phase shows that the improved selectivity has to be attributed to the control of substrate concentration.

Chemo-enzymatic synthesis of the active enantiomer of the anorressant 2- benzylmorpholine

Baker's yeast reduction of (Z)-α-bromocinnamaldehyde 1 in the presence of absorbing resins allows the easy preparation of the corresponding saturated bromo-alcohol 2 in high yields and enantiomeric excess. The absolute configuration is assigned through conversion into the (R)-phenyl oxirane 3 and 1-phenyl-2-propanol 4 of (S) absolute configuration. The (R)- epoxide is transformed into 6, the pharmacologically active enantiomer of the appetite suppressant 2-benzylmorpholine, to which the (R) configuration is assigned.