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Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R)-3-hydroxy-2-methyl-3-(4-nitrophenyl)propanal is used as a potential pharmaceutical compound due to the presence of the nitrophenyl group, which may impart pharmacological activity. Its unique structure and chiral centers could contribute to the development of new drugs.
Used in Organic Chemistry:
(2S,3R)-3-hydroxy-2-methyl-3-(4-nitrophenyl)propanal is used as a potential candidate for asymmetric synthesis, a technique in organic chemistry that allows for the selective production of one enantiomer of a chiral compound. This can lead to the development of new synthetic pathways for other compounds.

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 123-38-6 propionaldehyde 
• 1693-71-6 tris(allyl)borate 

Downstream Products

• 1233346-28-5 (1R,2S)-2-methyl-1-(4-nitrophenyl)propane-1,3-diol 
• 1034621-28-7 (1S,2R)-2-methyl-1-(4-nitrophenyl)propane-1,3-diol 

Relevant academic research and scientific papers

Titanium Alkoxide-Based Regioselective Alkyne-Alkyne Reductive Coupling Mediated by in Situ Generated Arylamidate

Titanium alkoxide-based alkyne-alkyne reductive coupling mediated by in situ generated arylamidate is described. A high level of regioselectivity is achieved in 37 examples, where (E,E)-dienes are exclusively formed. To the best of our knowledge, this stu

Multifunctional heterocyclic scaffolds for hybrid Lewis acid/Lewis base catalysis of carbon–carbon bond formation

Several new classes of hybrid catalysts have been synthesized by tethering heterocyclic metal (Lewis acid) chelating scaffolds to several different amines capable of facilitating enamine catalysis. Oxazole, thiazole, and imidazole-based chiral precatalyst

Design and Synthesis of Oxazoline-Based Scaffolds for Hybrid Lewis Acid/Lewis Base Catalysis of Carbon-Carbon Bond Formation

A new class of hybrid Lewis acid/Lewis base catalysts has been designed and prepared with an initial objective of promoting stereoselective direct aldol reactions. Several scaffolds were synthesized that contain amine moieties capable of enamine catalysis

(1,2-Diaminoethane-1,2-diyl)bis(N-methylpyridinium) Salts as a Prospective Platform for Designing Recyclable Prolinamide-Based Organocatalysts

A new efficient and highly recyclable organocatalyst has been developed for asymmetric cross-aldol reactions under neat conditions in ketone-ketone, ketone-aldehyde, and aldehyde-aldehyde systems. The catalyst features two prolinamide fragments and a Csu

Prolinamide-Derived Ionic-Liquid-Supported Organocatalyst for Asymmetric Mono- and Bis-Aldol Reactions in the Presence of Water

A novel recyclable prolinamide-derived ionic-liquid-supported organocatalyst of asymmetric cross-aldol reactions in aqueous medium has been developed. In its presence, aromatic aldehydes react with cyclic or linear ketones to afford chiral aldol adducts i

Rh-catalyzed aldehyde - Aldehyde cross-aldol reaction under base-free conditions: In situ aldehyde-derived enolate formation through orthogonal activation

The chemoselective generation of aldehyde-derived enolates to realize an aldehyde - aldehyde cross-aldol reaction is described. A combined Rh/dippf system efficiently promoted the isomerization/aldol sequence by using primary allylic, homoallylic, and bishomoallylic alcohols; secondary allylic and homoallylic alcohols; and trialkoxyboranes that were derived from primary allylic and homoallylic alcohols. The reaction proceeded at ambient temperature under base-free conditions, thus giving cross-aldol products with high chemoselectivity. Mechanistic studies, as well as its application to double-aldol processes under protecting-group-free conditions, are also described. Copyright

Recoverable silica-gel supported binam-prolinamides as organocatalysts for the enantioselective solvent-free intra- and intermolecular aldol reaction

Silica-gel supported binam-derived prolinamides are efficient organocatalysts for the direct intramolecular and intermolecular aldol reaction under solvent-free conditions using conventional magnetic stirring. These organocatalysts in combination with benzoic acid showed similar results to those obtained under similar homogeneous reaction conditions using an organocatalyst of related structure. For the intermolecular process, the aldol products were obtained at room temperature and using only 2 equiv of the ketone with high yields, regio-, diastereo- and enantioselectivities. Under these reaction conditions, also the cross aldol reaction between aldehydes is possible. The recovered catalyst can be reused up to nine times providing similar results. More interestingly, these heterogeneous organocatalysts can be used in the intramolecular aldol reaction allowing the synthesis of the Wieland-Miescher and ketone analogues with up to 92% ee, with its reused being possible up to five times without detrimental on the obtained results.

Rhodium-catalyzed cross-aldol reaction: In situ aldehyde-enolate formation from allyloxyboranes and primary allylic alcohols

Dip in. A Rh/dippf catalyst generates aldehyde-derived enol boranes at ambient temperature by isomerization of allyloxy- and homoallyloxyboranes. A one-pot isomerization/cross-aldol sequence provides aldehyde-aldehyde adducts in good yield with syn select

Rhodium-catalyzed cross-aldol reaction: In situ aldehyde-enolate formation from allyloxyboranes and primary allylic alcohols

Dip in! A Rh/dippf catalyst generates aldehyde-derived enol boranes at ambient temperature by isomerization of allyloxy- and homoallyloxyboranes. A one-pot isomerization/cross-aldol sequence provides aldehyde-aldehyde adducts in good yield with syn select

Cross-linked-polymer-supported N-{2'-[(Arylsulfonyl)amino][1,1'- binaphthalen]-2-yl}prolinamide as organocatalyst for the direct aldol intermolecular reaction under solvent-free conditions

A bottom-up strategy was used for the synthesis of cross-linked copolymers containing the organocatalyst N-{(1R)-2'-{[(4-ethylphenyl)sulfonyl]amino}[1,1'- binaphthalen]-2-yl}-D-prolinamide derived from 2 (Scheme 1). The polymer-bound catalyst 5b containin