70982-75-1

Upstream product

• 103-82-2 phenylacetic acid 
• 1068-55-9 isopropylmagnesium chloride 
• 114-70-5 sodium phenylacetate 
• 123-38-6 propionaldehyde 
• 40596-15-4 (3RS,4RS)-4-phenyl-5-hexen-3-ol 
• 31491-21-1 2-phenyl-1,1-bis(trimethylsilyloxy)ethene 
• 40596-15-4 (3R,4S)-4-Phenyl-hex-5-en-3-ol 

Downstream Products

• 91213-61-5 (+/-)-erythro-2-cyclohexyl-3-hydroxy-valeric acid 
• 100939-27-3 α-(1-Hydroxypropyl)benzenessigsaeure-methylester 
• 1560-09-4 (Z)-but-1-en-1-ylbenzene 
• 1005-64-7 trans-1-phenyl-1-butene 
• 1035953-92-4 4-Ethyl-3-phenyl-oxetan-2-one 
• 20055-52-1 α-(1-Hydroxypropyl)benzenessigsaeure-methylester 
• 70982-84-2 trans-4-Ethyl-3-phenyl-2-oxetanon 

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.