352438-06-3

Upstream product

• 937204-00-7 C₂₄H₃₉NO₄Si 
• 5680-79-5 glycine ethyl ester hydrochloride 
• 170918-41-9 (S)-2-amino-3-phenyl-1,1-dimethylpropanol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1360703-42-9 2-methyl-4-phenylbut-3-yn-2-yl benzoylcarbamate 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 168297-97-0 (S)-4-benzyl-5,5-dimethyl-N-(3-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 1527484-91-8 C₁₈H₂₅NO₄ 
• 1527484-89-4 C₂₂H₂₅NO₅ 
• 75-16-1 methylmagnesium bromide 
• 320606-07-3 (S)-3-(2'-benzyl-3'-phenylpropionyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 250280-60-5 (4S)-4-Benzyl-5,5-dimethyl-3-[(2S)-2-methyl-6-heptenoyl]-1,3-oxazolidin-2-one 
• 168297-81-2 N-<(S)-1-benzyl-2-hydroxy-2-methylpropyl>-2,2,2-trichloroethanamide 

Downstream Products

• 168297-89-0 (S)-3-(2',2'-dimethyl-1'-oxopropyl)-4-benzyl-5,5-dimethyloxazolidin-2-one 
• 1527484-57-6 (S)-4-benzyl-5,5-dimethyl-N-[(S)-2-(1-(2,2,6,6-tetramethylpiperidinyl)oxy)propanoyl]-1,3-oxazolidin-2-one 
• 1527484-58-7 (S)-4-benzyl-5,5-dimethyl-N-[(R)-2-(1-(2,2,6,6-tetramethylpiperidinyl)oxy)propanoyl]-1,3-oxazolidin-2-one 
• 1527484-95-2 (S)-4-benzyl-N-(5-hexynoyl)-5,5-dimethyl-1,3-oxazolidin-2-one 
• 1647060-99-8 (S)-4-benzyl-5,5-dimethyl-N-[(S)-2-hydroxypropanoyl]-1,3-oxazolidin-2-one 
• 1647060-90-9 (S)-4-benzyl-N-(2-cyclopropylacetyl)-5,5-dimethyl-1,3-oxazolidin-2-one 
• 1527484-94-1 (S)-4-benzyl-N-(5-hexenoyl)-5,5-dimethyl-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Synthesis of enantioenriched α-chiral bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficie

Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates

Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.

Stereoselective Oxidation of Titanium(IV) Enolates with Oxygen

A novel approach to synthesize enantiomerically pure α-hydroxy carboxylic derivatives is reported. A highly stereoselective oxidation of titanium(IV) enolates from chiral N -acyloxazolidinones is performed with oxygen under simple experimental conditions

Asymmetric radical addition of TEMPO to titanium enolates

A mild method for a-hydroxylation of N-acyl oxazolidinones by asymmetric radical addition of the 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO) radical to titanium enolates was developed. The high diastereoselectivity and broad scope of the reaction show synthetic utility for the a-hydroxylation of substrates that are not tolerant to strongly basic conditions.

N -heterocyclic carbene catalyzed domino cyclization of propargylic alcohols and benzoyl isocyanates

N-Hetereocyclic carbenes (NHCs) were found to be efficient catalysts for the cyclization of propargylic alcohols and isocyanates. Domino cyclization reactions were carried out using isopropyl-substituted imidazolium salt as a precatalyst, and a wide range

A simple method for asymmetric trifluoromethylation of N-acyl oxazolidinones via Ru-catalyzed radical addition to zirconium enolates

A Ru-catalyzed direct thermal trifluoromethylation and perfluoroalkylation of N-acyloxazolidinones has been developed. The reaction is experimentally simple and requires inexpensive reagents while providing good yields of products with good levels of stereocontrol. Preliminary studies have shown notable compatibility with functional groups, aromatics, and certain heteroaromatic substituents. The described method provides a useful alternative for the synthesis of fluorinated materials in an experimentally convenient manner.

Catalytic enantioselective Steglich rearrangements using chiral N-heterocyclic carbenes

The evaluation of a range of enantiomerically pure NHCs, prepared in situ from imidazolinium or triazolium salt precatalysts, to promote the catalytic enantioselective Steglich rearrangement of oxazolyl carbonates to their C-carboxyazlactones, is reported. Modest levels of enantioselectivity (up to 66% ee) are observed using oxazolidinone derived NHCs.

Enantioselective preparation of P-chiral phosphine oxides

A highly efficient chiral auxiliary-based strategy for the asymmetric synthesis of P-chiral phosphine oxides in >98:2 er has been developed. The methodology involves the highly stereoselective formation of P-chiral oxazolidinones that then undergo displacement with a variety of Grignard reagents to prepare the desired phosphine oxides.

Synthesis of azide-alkyne fragments for 'click' chemical applications. formation of chiral 1,4-disubstituted-(β-alkyl) γ- 1,2,3-triazole scaffolds from orthogonally protected chiral β-alkyl-trialkylsilyl γ- Pentynyl azides and chiral β-alkyl γ- Pentynyl-alcohols

A library of chiral γ-pentynyl alcohols and γ-pentynyl azides was made using the SuperQuat auxiliary. Coupling of the free alkynes with the azides by Huisgen 1,3-dipolar cycloaddition provided chiral oligomeric 1,4-disubstituted-1,2,3-triazoles as possible peptidomimetic compounds.

A temporary stereocentre approach for the asymmetric synthesis of chiral cyclopropane-carboxaldehydes

A novel way of combining chiral auxiliaries and substrate directable reactions is described that employs a three-step sequence of aldol/cyclopropanation/retro-aldol reactions for the asymmetric synthesis of enantiopure cyclopropane-carboxaldehydes. In the first step, reaction of the boron enolate of (S)-N-propionyl-5,5-dimethyl-oxazolidin-2-one with a series of α,β-unsaturated aldehydes affords their corresponding syn-aldol products in high de. In the second step, directed cyclopropanation of the alkene functionalities of these syn-aldols occurs under the stereodirecting effect of their 'temporary'β-hydroxyl stereocentres to give a series of cyclopropyl-aldols in high de. Finally, retro-aldol cleavage of the lithium alkoxide of these cyclopropyl-aldols results in destruction of their temporary β-hydroxy stereocentres to afford the parent chiral auxiliary and chiral cyclopropane-carboxaldehydes in >95% ee. The potential of this methodology has been demonstrated for the asymmetric synthesis of the cyclopropane containing natural product cascarillic acid in good yield.