117248-08-5

Upstream product

• 100-52-7 benzaldehyde 
• 107-92-6 butyric acid 
• 117037-11-3 (4R,5S)-3-[(R)-2-((R)-Hydroxy-phenyl-methyl)-butyryl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 117037-10-2 (S)-4-Benzyl-3-{(S)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-pentanoyl}-oxazolidin-2-one 
• 86294-73-7 2-(Trimethylsilyl)-butansaeure-trimethylsilylester 
• 85287-67-8 2,2,6,6-tetramethyl-4-propylidene-3,5-dioxa-2,6-disilaheptane 
• 24744-97-6 2-(α-hydroxy-benzyl)-butyric acid ethyl ester 

Downstream Products

• 14367-05-6 methyl 2-ethyl-3-hydroxy-3-phenylpropionate 
• 1560-09-4 (Z)-but-1-en-1-ylbenzene 
• 1005-64-7 trans-1-phenyl-1-butene 
• 82575-10-8 3-Ethyl-4-phenyl-oxetan-2-one 
• 14367-05-6 methyl 2-ethyl-3-hydroxy-3-phenylpropionate 
• 82575-10-8 (+/-)-trans-4-Ethyl-4-phenyl-2-oxetanone 
• 108146-96-9 (1'R,2R)-2-(hydroxyphenylmethyl)butyric acid methyl ester 

Relevant academic research and scientific papers

Asymmetric solution-phase mixture aldol reaction using oligomeric ethylene glycol tagged chiral oxazolidinones

Sorting tags are oligomeric structures that can be used as protecting groups or chiral auxiliaries enabling solution-phase mixture syntheses of multiple tagged compounds in one pot and allowing for facile and predictable chromatographic separation of products at the end of synthetic sequences. Perfluorinated hydrocarbon and oligomeric ethylene glycol (OEG) derivatives are known classes of sorting tags. Herein we describe the preparation of OEGylated chiral oxazolidinones and their use in asymmetric solution-phase mixture aldol reactions. Through the use of such oxazolidinones based on tyrosine four different individually tagged aldol adducts were obtained as a mixture, chromatographically demixed, detagged, and it was shown that these processes gave the desired aldol products in good yield and enantioselectivity.

CONTRASTERIC CARBOXIMIDE HYDROLYSIS WITH LITHIUM HYDROPEROXIDE

The use of lithium hydroperoxide for the highly regioselective hydrolysis of a range of carboximides is described.Numerous cases are provided where the regioselectivities exhibited by this reagent are dramatically different than the complementary reactions with hydroxide.

ERYTHRO SELECTIVE CROSS ALDOL REACTION VIA α-SILYL TRIMETHYLSILYL ESTERS.

Various fluoride ion mediated reactions of aliphatic α-silyl trimethylsilyl esters 1 with benzaldehyde have been investigated.Moderate erythro stereoselectivity is observed.

Stereochemistry of the Addition of Carboxylic Acid Dianions to Aldehydes under Kinetic and Thermodynamic Control - Synthesis and Configurational Assignment of 2,3-Disubstituted threo- and erythro-3-Hydroxycarboxylic Acids

Under kinetically controlled conditions (-50 deg C, 10 min) the carboxylic dianions 2 add to aldehydes 3 to give the threo/erythro-adducts 4/5 (Scheme 1); the threo-selectivity markedly increases with the bulkiness of the substituents of 2 or 3 and decreases with the charge/radius ratio of the counter-ions of 2.From these results a syn-transition state with a HOMO-LUMO ineraction between 2 and 3 is derived (Scheme 3).For appropriate substituents a far higher threo-selectivity is observed under thermodynamically (22-50 deg C, 1-3 days) than under kinetically controlled conditions.We describe the isolation of the hydroxy acids 6 and 7, which are formed from 4 and 5 on acidic hydrolysis, and show how their configurations can be unambiguously assigned on the basis of 1H-NMR data.