14367-04-5

Upstream product

• 24744-97-6 2-(α-hydroxy-benzyl)-butyric acid ethyl ester 
• 100-52-7 benzaldehyde 
• 107-92-6 butyric acid 
• 86294-73-7 2-(Trimethylsilyl)-butansaeure-trimethylsilylester 
• 85287-67-8 2,2,6,6-tetramethyl-4-propylidene-3,5-dioxa-2,6-disilaheptane 

Downstream Products

• 1005-64-7 trans-1-phenyl-1-butene 
• 82575-10-8 (+/-)-trans-4-Ethyl-4-phenyl-2-oxetanone 
• 14367-05-6 methyl 2-ethyl-3-hydroxy-3-phenylpropionate 
• 1560-09-4 (Z)-but-1-en-1-ylbenzene 
• 82575-10-8 3-Ethyl-4-phenyl-oxetan-2-one 
• 14367-05-6 methyl 2-ethyl-3-hydroxy-3-phenylpropionate 

Relevant academic research and scientific papers

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.