33398-52-6

Upstream product

• 69974-12-5 trans-4-tert-Butyl-3-phenyl-2-oxetanon 
• 103-82-2 phenylacetic acid 
• 630-19-3 pivalaldehyde 
• 620-23-5 m-tolyl aldehyde 
• 31491-21-1 2-phenyl-1,1-bis(trimethylsilyloxy)ethene 
• 87383-87-7 trans-2,2-dimethyl-4-phenylhex-5-en-3-ol 
• 104-87-0 4-methyl-benzaldehyde 
• 33398-52-6 α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure 
• 87383-87-7 2,2-dimethyl-4-phenyl-5-hexen-3-ol 
• 33398-52-6 erythro-3-Hydroxy-4,4-dimethyl-2-phenylvaleriansaeure 

Downstream Products

• 75245-37-3 threo-3-Hydroxy-2-phenyl-3-(m-tolyl)propionsaeure 
• 33398-52-6 erythro-3-Hydroxy-4,4-dimethyl-2-phenylvaleriansaeure 
• 33398-50-4 α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure-methylester 
• 33398-52-6 α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure 
• 33398-50-4 α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure-methylester 
• 82575-16-4 α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure-tert-butylester 
• 82575-14-2 α-(1-Hydroxy-2,2-dimethylpropyl)benzenessigsaeure-ethylester 
• 82584-39-2 (2R,3S)-3-Hydroxy-4,4-dimethyl-2-phenyl-pentanoatetetramethyl-ammonium; 
• 3846-66-0 (E)-1-tert-butyl-2-phenylethene 

Relevant academic research and scientific papers

ERYTHROSELECTIVITY IN ADDITION OF γ-SUBSTITUTED ALLYLSILANES TO ALDEHYDES IN THE PRESENCE OF TITANIUM CHLORIDE

(E)-Crotyltrimethylsilane and (E)-cinnamyltrimethylsilane were allowed to react with aldehydes (RCHO: t-Bu, i-Pr, Et, Me) in the presence of titanium chloride to give erythro homoallyl alcohols with over 93percent selectivity.Lower erythroselectivity was observed in the reaction of (Z)-allylsilanes.

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.