Bromide ion → N-(1-(1,4-dioxaspiro[4.5]decan-8-yl)but-3-en-1-yl)-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

A solution (E)-N-(1,4-dioxaspiro[4.5]decan-8-ylmethylene)-2-methylpropane-2-sulfinamide (1.91 g, 6.99 mmol), prepared in the previous step, in dry THF (48 mL) was treated with a solution of allylmagnesiumm bromide (10.5 mL, 21 mmol, 2N in THF) dropwise at ambient temperature under argon. After the complete addition, the reaction mixture was allowed to stir at room temperature and for 3 hours and then quenched at 0° C. by the cautious addition of saturated ammonium chloride solution. After extraction with ethyl acetate, the organic layer was concentrated in vacuo and the residue purified by flash chromatography (silica gel, 0-5% MeOH/Ethyl Acetate) to afford the product as a mixture of disatereomers.

Provenance & Evidence