Diastereoselective α-alkylation of β-hydroxycarboxylic esters through alkoxide enolates: diethyl (2S, 3R)-(+)-3-allyl-2-hydroxysuccinate from diethyl (S)-(−)-malate

CAS index name: Butanedioic acid, 2-hydroxy-3-(2-propenyl)-, diethyl ester, [S-(R,S)]

Organic Syntheses

Reaction scheme of Diastereoselective α-alkylation of β-hydroxycarboxylic esters through alkoxide enolates: diethyl (2S, 3R)-(+)-3-allyl-2-hydroxysuccinate from diethyl (S)-(−)-malate from Organic Syntheses
Scheme as published in Org. Synth. Coll. Vol. 7, p. 153; Vol. 63, p. 109.

A checked procedure from Organic Syntheses, the journal whose preparations are repeated in a second laboratory before publication. The full experimental, with amounts, hazards and characterisation data, is on orgsyn.org.

Reagents

CompoundRoleEquivMW (g/mol)ρ (g/mL)Safety
Butane106-97-8 · C4H10 product — 58.12 — Flammable (GHS02)Compressed Gas (GHS04)Danger

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