A simple and direct synthesis of α-hydroxy unsaturated aldehydes from α-cyano-α-hydroxymethyl epoxides

L Khamliche, A Robert

Index: Khamliche, Layachi; Robert, Albert Journal of the Chemical Society, Chemical Communications, 1987 , p. 1869 - 1870

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Abstract

The ring opening of a-cyano-a-hydroxymethyl epoxides by a solution of the complex LipNiBr4 in tetrahydrofuran leads to a-bromo-a'-hydroxy ketones which in treatment with pyridine give good yields of a-hydroxy unsaturated a Ide h ydes. ... Scheme 1. Reagents and conditions: i, epoxide (1) (5.7 mmol), Li2NiBr4 (2.85 mmol), THF (27 ml), room temp., 6 h under Nz; ii, H,O; iii, pyridine (5.7 mmol), reflux, 2 h. ... Published on 01 January 1987. Downloaded by ...