934237-46-4

Upstream product

• 3426-71-9 Benzyl N-hydroxycarbamate 
• 104-55-2 3-phenyl-propenal 
• 909019-16-5 benzyl (tert‐butyldimethylsilyl)oxycarbamate 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 83649-47-2 (S)-(-)-β-Phenyl-β-alanine hydrochloride 
• 614-19-7 (S)-3-amino-3-phenylpropanoic acid 
• 934237-57-7 (-)-(3S)-2-(benzyloxycarbonyl)-3-phenylisoxazolidin-5-one 

Relevant academic research and scientific papers

Spiro-Pyrrolidine-Catalyzed Asymmetric Conjugate Addition of Hydroxylamine to Enals and 2,4-Dienals

A spiro-pyrrolidine-catalyzed tandem aza-1,4-addition/hemi-acetalization reaction was developed with excellent enantioselectivity (12 examples of ≥99% ee), and several substrates proceeded with higher ee (up to 10% increase) compared with the literature data. Particularly, an interesting and unusual aza-1,6-/oxa-1,4-addition for some substrates was also observed.

Organocatalytic synthesis of 5-hydroxyisoxazolidine catalyzed by camphor sulfonyl hydrazines through aza-Michael addition/cyclization

A series of chiral 5-hydroxy isoxazolidines has been successfully synthesized through camphor sulfonyl hydrazine-catalyzed asymmetric aza-Michael addition reaction between N,O-protected hydroxyamines and enals. Moderate yields with moderate to good enantioselectivities (up to 96% enantiomeric excess [ee]) were achieved. It provides an alternative asymmetric approach to preparing isoxazolidine derivatives.

Immobilization of cis-4-Hydroxydiphenylprolinol Silyl Ethers onto Polystyrene. Application in the Catalytic Enantioselective Synthesis of 5-Hydroxyisoxazolidines in Batch and Flow

A new family of polystyrene-supported cis-4-hydroxydiphenylprolinol silyl ethers has been prepared, and the resulting polymers have been evaluated as organocatalysts to promote the tandem reaction between N-protected hydroxylamines and α,β-unsaturated aldehydes in batch and flow. The new PS-supported catalysts compare favorably with well-established immobilized J?rgensen-Hayashi catalysts, affording 5-hydroxyisoxazolidines as single diastereoisomers with high enantioselectivities and good yields (up to 83% yield, up to 99% ee). (Figure presented.).

Chiral ionic liquid/ESI-MS methodology as an efficient tool for the study of transformations of supported organocatalysts: Deactivation pathways of jorgensen-hayashi-type catalysts in asymmetric Michael reactions

The deactivation pathways of Jorgensen-Hayashi-type organocatalysts modified with an ionic liquid fragment in asymmetric Michael reactions of α,β-enals with C- (nitromethane, dimethylmalonate) or N-nucleophiles (N-carbobenzyloxyhydroxylamine) that involve

Asymmetric synthesis of maraviroc (UK-427,857)

The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.

Catalytic enantioselective 5-hydroxyisoxazolidine synthesis: An asymmetric entry to β-amino acids

The highly chemo- and enantioselective organocatalytic tandem reaction between N-carbamate-protected hydroxylamines and α,β-unsaturated aldehydes is presented. The reaction represents a unique entry for the asymmetric synthesis of 5-hydroxyisoxazolidines, oxazolidin-5-ones or γ-hydroxyamino alcohols in high yields and 90-99% ee. A procedure for the conversion of the oxazolidin-5-ones into the corresponding β-amino acids is also described. Georg Thieme Verlag Stuttgart.

Organocatalytic asymmetric 5-hydroxyisoxazolidine synthesis: A highly enantioselective route to β-amino acids

The highly chemo- and enantioselective organocatalytic tandem reaction between N-protected hydroxyl amines and α,β-unsaturated aldehydes is presented; the reaction provides access to 5-hydroxyisoxazolidines and β-amino acids in high yields and with 90-99% ee. The Royal Society of Chemistry.