191109-48-5

Usage

Uses

Used in Organic Synthesis:
(S)-b-AMino-4-Methoxy-benzeneethanol is used as a chiral auxiliary in the field of organic synthesis for [application reason] its ability to influence the stereochemistry of the reactions it participates in, leading to the formation of desired enantiomers with high selectivity.
Used in Pharmaceutical Production:
In the pharmaceutical industry, (S)-b-AMino-4-Methoxy-benzeneethanol is used as a building block for [application reason] its chiral nature, which is essential in the development of new drugs and other biologically active compounds that require specific stereochemistry for their therapeutic effects.
Used in Asymmetric Catalysis:
(S)-b-AMino-4-Methoxy-benzeneethanol is also utilized in the field of asymmetric catalysis as a [application type] for [application reason] its potential to enhance the selectivity and efficiency of catalytic reactions, contributing to the production of enantiomerically pure compounds.
Used in Enantiomerically Pure Pharmaceutical Production:
Furthermore, (S)-b-AMino-4-Methoxy-benzeneethanol is employed in the production of enantiomerically pure pharmaceuticals as a [application type] for [application reason] its ability to serve as a key component in the synthesis of such pharmaceuticals, ensuring the correct stereochemistry for optimal therapeutic activity and minimizing potential side effects associated with the wrong enantiomer.

Upstream product

• 1242430-53-0 (S)-2-[(methoxycarbonyl)amino]-2-(4-methoxyphenyl)-1-ethanol 
• 24593-48-4 (2S)-2-amino-2-(4-methoxyphenyl)acetic acid 
• 637-69-4 4-Methoxystyrene 
• 191109-43-0 (R)-4-(p-methoxyphenyl)-1,3-dioxolane-2-one 
• 13603-63-9 (R)-1-(4-methoxyphenyl)ethane-1,2-diol 
• 191109-46-3 (S)-2-azido-2-(p-methoxyphenyl)ethanol 

Downstream Products

• 1242430-45-0 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-3-methyl-1H-pyrrol-2(5H)-one 
• 1268344-85-9 1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 1268345-08-9 (S)-5-benzyl-1-[(S)-2-hydroxy-1-(4-methoxyphenyl)ethyl]-4-methoxy-1H-pyrrol-2(5H)-one 
• 191109-56-5 2-(Bis-{[(S)-2-hydroxy-1-(4-methoxy-phenyl)-ethylcarbamoyl]-methyl}-amino)-N-[(S)-2-hydroxy-1-(4-methoxy-phenyl)-ethyl]-acetamide 

Relevant academic research and scientific papers

Asymmetric Allylic C-H Alkylation via Palladium(II)/ cis-ArSOX Catalysis

We report the development of Pd(II)/cis-aryl sulfoxide-oxazoline (cis-ArSOX) catalysts for asymmetric C-H alkylation of terminal olefins with a variety of synthetically versatile nucleophiles. The modular, tunable, and oxidatively stable ArSOX scaffold is key to the unprecedented broad scope and high enantioselectivity (37 examples, avg. > 90% ee). Pd(II)/cis-ArSOX is unique in its ability to effect high reactivity and catalyst-controlled diastereoselectivity on the alkylation of aliphatic olefins. We anticipate that this new chiral ligand class will find use in other transition metal catalyzed processes that operate under oxidative conditions.

Total Synthesis of (-)-Rhazinilam and Formal Synthesis of (+)-Eburenine and (+)-Aspidospermidine: Asymmetric Cu-Catalyzed Propargylic Substitution

A total synthesis of (-)-rhazinilam and formal syntheses of (+)-eburenine and (+)-aspidospermidine that rely on a copper(I)-catalyzed asymmetric propargylic substitution as the key step are reported. A salient feature of the reaction is the asymmetric con

TRICYCLIC GUANIDINE DERIVATIVE

Disclosed are compounds useful as inhibitors of Phosphodiesterase 1 (PDE1), compositions thereof, and methods of using the same.

TRICYCLIC DERIVATIVE

Disclosed are compounds useful as inhibitors of phosphodiesterase 1 (PDE1), compositions thereof, and methods of using the same.

Asymmetric synthesis via aziridinium ions: Exploring the stereospecificity of the ring opening of aziridinium ions and a formal synthesis of (-)-swainsonine

The use of aziridinium ions in two different projects is described. First, the stereospecificity of the ring opening of aziridinium ions with MeNH 2 as a route to chiral diamines has been explored. When the aziridinium ion contained a phenyl or para-methoxyphenyl substituent, stereospecific ring opening occurred. In contrast, switching the para-methoxy group to a para-N,N-dimethylamino group gave a racemic diamine product. Second, starting from N-Boc pyrrolidine, asymmetric lithiation-trapping-ring expansion (via an aziridinium ion) was used to synthesise a piperidine alcohol. In this way, a formal synthesis of (-)-swainsonine was completed.

The first enantioselective synthesis of cytotoxic marine natural product palau'imide and assignment of its C-20 stereochemistry

Methyl tetramate derivative 6 has been developed as a new building block for the flexible and racemization-free synthesis of methyl 5-benzyl-3- methyltetramate via alkylation, and used in the first asymmetric synthesis of palau'imide (1). This allowed the establishment of the hitherto unknown stereochemistry at the C-20 of palau'imide as S.

Asymmetric aminohydroxylation of substituted styrenes: Applications in the synthesis of enantiomerically enriched arylglycinols and a diamine

The catalytic asymmetric aminohydroxylation of a variety of styrene derivatives and vinyl aromatics using osmium tetroxide in conjunction with alkaloid-derived ligands [e.g. (DHQ)2PHAL or (DHQD)2-PHAL] and haloamine salts of alkyl carbamates (e.g. ethyl carbamate or tert-butyl carbamate) has been investigated. By observing the effect of different aromatic substituents and alkyl carbamates on the regioselectivity, yield and enantioselectivity of the aminohydroxylation reactions, a number of conclusions have been reached: (i) the 1-aryl-2-hydroxyethylamine regioisomers were obtained as the major products in reasonable yield and high (≤87%) enantiomeric excess; (ii) tert-butyl carbamate was superior to ethyl carbamate in terms of yield, enantioselectivity and ease of removal of the N-protecting group; (iii) high (≥96%) enantioselectivity was observed with a 4-methoxy-substituted styrene whereas ortho-substituted styrenes gave lower enantioselectivities; (iv) chiral ligands (DHQ)2PHAL and (DHQD)2PHAL gave essentially equal and opposite senses and degrees of asymmetric induction; (v) regioselectivity was ligand dependent with better regioselectivity (and therefore higher isolated yields) obtained with (DHQ)2PHAL than with (DHQD)2PHAL. The products of the aminohydroxylation reactions were used to prepare enantiomerically enriched arylglycinols and a chiral diamine.

Enantioselective allylic oxidation of cycloalkenes by using Cu(II)-tris(oxazoline) complex as a catalyst

Optically active copper(II)-tris(oxazoline) complex that was synthesized as a model compound of the active site of non-heme oxygenase, was found to catalyze allylic oxidation of cycloalkenes to give the corresponding 2-cycloalkenyl benzoates with moderate to excellent enantioselectivity (up to 93% ee) under die Kharash-Sosnovsky reaction conditions.