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Direct indium-promoted preparation of α-methylene-γ-lactones from 2-(bromomethyl)acrylic acid and carbonyl compounds

✍ Scribed by Prabir K Choudhury; Francisco Foubelo; Miguel Yus

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
500 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

The reaction of 2-(bromomethyl)acrylic acid (2) with different carbonyl compounds 1 [CH20, (E)-CH3CH=CHCHO, iprCHO, tBuCHO, PhCHO, CH3(CH2)sCHO, c-C6HIlCHO, Ph2CHCHO, (CH2)5CO, furfural, 1,4-cyclohexanedione, 2-chlorocyclohexanone, 2-hydroxybenzaldehyde, phthaldehyde, N-Boc-3-indolecarboxaldehyde, cholestanone, (1R)-(-)-myrtenal] and indium powder in a l:l THF:H20 mixture at room temperature affords, after acidic work-up with 6M hydrochloric acid, the corresponding et-methylene-T-lactones 3.

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The reaction of 2-(bromomethyl)acrylic acid (1) with different carbonyl compounds (2) [CH20, (E)-CH3CH=CHCHO, PriCHO, ButCHO, PhCHO, CH3(CH2)5CHO, c-C6HllCHO, Ph2CHCHO, (CH2)sCO] and indium powder in a 1:1 THF:H20 mixture at room temperatme affords, after acidic work-up with hydiochloric acid, the c