74143-99-0Relevant academic research and scientific papers
Mild, effective and regioselective ring-opening of oxiranes using several thiosilanes promoted by tetrabutylammonium fluoride as catalyst
Tanabe, Yoo,Mori, Kei,Yoshida, Yoshihiro
, p. 671 - 675 (2007/10/03)
The smooth and regioselective ring-opening of oxiranes with isothiocyanatotrimethylsilane 1 (TMSNCS), O-trimethylsilyl thioacetate 2 (TMSOCSMe) and phenylthiotrimethylsilane 3 (TMSSPh) proceeds under mild conditions promoted by 0.02 equiv. of TBAF (tetrabutylammonium fluoride) catalyst in a homogeneous system. In most cases, the TBAF catalyst works as an effective promoter. 1,2-Epoxyoctane 4, styrene oxide 5, glycidyl 4-(tert-butyl)benzoate 6,1,2-epoxycyclohexane 7, methyl epoxybutanoate 8 and (2R)-glycidyl toluene-p-sulfonate 14 undergo smooth ring-opening in moderate to high yields. When ambiphilic TMSNCS 1 and TMSOCSMe 2 are used as reactants, the sulfur position exclusively attacks the oxiranes. No substantial thiirane formation and/or decyanation occurs when 1 is used. Deacetylation also fails to occur when 2 is used.
Preparation of β-Hydroxy-α-phenylthio Esters via Condensation of Aldehydes with α-Phenylthio Ester Enolate Anions
Hoye, Thomas R.,Kurth, Mark J.
, p. 3549 - 3554 (2007/10/02)
The lithium enolates of α-phenylthio esters 5 react with aldehydes 6 to give good yields of diastereomeric aldol products 7 and 8 provided that anhydrous zinc chloride is first added to the enolate solution.The threo or erythro nature of several of the al
