STEREOSELECTIVE SYNTHESIS OF (E)-2-ALKENE-1,4-DIOLS VIA METALLATED ALLYLIC SULPHOXIDES

DOI: 10.1016/S0040-4020(01)82095-0

Source and publish data:

Tetrahedron p. 5443 - 5450 (1986)

Update date:2022-09-26

Topics:

Authors:

Annunziata, Rita

Cinquino, Mauro

Cozzi, Franco

Raimondi, Laura

Stefanelli, Stefania

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Article abstract of DOI:10.1016/S0040-4020(01)82095-0

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.

Full text of DOI:10.1016/S0040-4020(01)82095-0

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