58113-93-2

Upstream product

• 31469-23-5 2-(tert-butyl)-1,1-bis(trimethylsilyloxy)ethene 
• 100-52-7 benzaldehyde 
• 1070-83-3 tert-Butylacetic acid 
• 73378-20-8 cis-3-tert-butyl-4-phenyloxetan-2-one 
• 73378-21-9 trans-3-tert-butyl-4-phenyloxetan-2-one 

Downstream Products

• 3846-66-0 (E)-1-tert-butyl-2-phenylethene 
• 73378-21-9 trans-3-tert-butyl-4-phenyloxetan-2-one 
• 186521-97-1 3-tert-butyl-4-phenyloxetan-2-one 
• 14367-06-7 methyl 2-t-butyl-3-hydroxy-3-phenylpropionate 
• 73378-20-8 cis-3-tert-butyl-4-phenyloxetan-2-one 

Relevant academic research and scientific papers

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.