cas 103867-69-2, (E)-2-Phenyl-6-(toluene-4-sulfinyl)-hex-5-en-3-ol

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Cram-selective Addition of α-Allyl Sulphinyl Anion to Chiral Aldehydes: Synthesis of (E)-1,4-Dihydroxyalk-2-enes
The stereoselective introduction of an allylic alcohol function into chiral aldehydes is readily achieved by sequential condensation of aldehydes with an allylic sulphinyl anion and thiophile-promoted desulphurization of the resulting α-substituted allylic sulphoxides.
Annunziata, Rita,Cinquini, Mauro,Cozzi, Franco,Raimondi, Laura
p. 366 - 367
(1986)
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STEREOSELECTIVE SYNTHESIS OF (E)-2-ALKENE-1,4-DIOLS VIA METALLATED ALLYLIC SULPHOXIDES
Reaction of allyl sulphinyl anion with chiral α-methylaldehydes affords α- or γ-adducts in highly regiocontrolled fashion, depending on reaction conditions.From the α-adducts syn (E)-2-alkene-1,4-diols are obtained as major (d.r. 2:1 28:1) products by thiophile promoted desulphurization.
Annunziata, Rita,Cinquino, Mauro,Cozzi, Franco,Raimondi, Laura,Stefanelli, Stefania
p. 5443 - 5450
(2007/10/02)