Reaction of allyl sulphinyl anion with chiral α-methylaldehydes affords α- or γ-adducts in highly regio-controlled 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.
STEREOSELECTIVE SYNTHESIS OF (E)-2-ALKENE-1,4-DIOLS VIA METALATED ALLYLIC SULFOXIDES / R. ANNUNZIATA, M. CINQUINI, F. COZZI, L. RAIMONDI, S. STEFANELLI. - In: TETRAHEDRON. - ISSN 0040-4020. - 42:19(1986), pp. 5443-5450.
STEREOSELECTIVE SYNTHESIS OF (E)-2-ALKENE-1,4-DIOLS VIA METALATED ALLYLIC SULFOXIDES
R. ANNUNZIATA;M. CINQUINI;F. COZZI;L. RAIMONDI;
1986
Abstract
Reaction of allyl sulphinyl anion with chiral α-methylaldehydes affords α- or γ-adducts in highly regio-controlled 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.
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