769167-84-2

Upstream product

• 95530-58-8 (R)-4-isopropyloxazolidin-2-one 
• 457602-59-4 2,3-diphenylbutyraldehyde 
• 1201351-70-3 (R)-N-(trimethylsilylmethyl)-4-isopropyloxazolidin-2-one 
• 2042-85-5 1,2-diphenylpropan-1-one 
• 457602-58-3 methyl β-phenyl-α-phenylbutyrate 
• 101-41-7 benzeneacetic acid methyl ester 
• 108774-24-9 2,3-diphenyl-1-butanol 
• 585-71-7 (1-bromoethyl)benzne 

Downstream Products

• 457602-66-3 4(R)-isopropyl-3-[(3S,4S)-4-phenyl-4-R-(1-phenylethyl)-[1,2]-dioxetan-3-yl]oxazolidin-2-one 
• 457602-68-5 (R)-3-((1S,2S,3R)-1,2-Dihydroxy-2,3-diphenyl-butyl)-4-isopropyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Temperature and solvent control of the stereoselectivity in the reactions of singlet oxygen with oxazolidinone-substituted enecarbamates

Oxazolidinone-functionalized enecarbamates react stereoselectively with singlet oxygen to give methyldesoxybenzoin (MDB) in moderate to high enantiomeric excess. The stereochemical outcome depends on the E/Z substrate geometry, temperature, and solvent variables. The analysis of the differential activation parameters suggests a large contribution from the entropy term in determining the enantioselectivity. We demonstrate the utility of the temperature and solvent variables in determining the degree of the photochemical kinetic resolution of the enecarbamates; for example, in the photooxygenation at -70 °C in methanol, MDB may be obtained in methanol. Copyright

Isolation and syn elimination of a peterson adduct to obtain optically pure product in the diastereoselective synthesis of oxazolidinone-functionalized enecarbamates

The Peterson reaction of (4R)-N-(trimethylsilyl)methyl-4-alkyloxazolidin-2- one gives (E/Z)-(4R)-N-(2', 3'- diphenylbut-1'-enyl)-4-alkyloxazolidin-2-ones (enecarbamates) with increasing (Z)-selectivity and moderate-to-high diastereoselectivity in the indi

Conformationally controlled (entropy effects), stereoselective vibrational quenching of singlet oxygen in the oxidative cleavage of oxazolidinone-functionalized enecarbamates through solvent and temperature variations

On photooxygenation (methylene blue as sensitizer) of E/Z enecarbamates, equipped with the oxazolidinone chiral auxiliary, the oxidative cleavage of the alkenyl functionality releases the enantiomerically enriched methyldesoxybenzoin (MDB) product. The ex

Highly diastereoselective dioxetane formation in the photooxygenation of enecarbamates with an oxazolidinone chiral auxiliary: Steric control in the [2 + 2] cycloaddition of singlet oxygen through conformational alignment

The photooxygenation of oxazolidinone-substituted enecarbamates leads to diastereomerically pure dioxetanes. The high diastereoselectivity is rationalized in terms of effective π-facial control achieved by shielding one side of the double bond with the ch