Hitherto unknown amide (III) is a suitable building block for the synthesis of vinyl ketones on a multigram scale via addition of Grignard reagents and subsequent oxidation.

Chemistry indexing and abstracting service

Weinreb Amide Based Building Block for Convenient Access to Vinyl Ketones.

A new strategy for the synthesis of vinyl ketones has been achieved. Hitherto unknown and easily accessible, β-phenylseleno-N-methoxy-N-methylpropanamide, obtained through two simple reactions, served as a building block for convenient access to vinyl ketones. The N-methoxy-N-methyl amide moiety ensured no overaddition of the Grignard reagent and, hence, the excellent formation of β-phenylseleno ketones; oxidative work-up with ­hydrogen peroxide provided ready access to the vinyl ketones with concomitant loss of phenylselanol.

Weinreb Amide Based Building Block for Convenient Access to Vinyl Ketones.

References

Weinreb Amide Based Building Block for Convenient Access to Vinyl Ketones

Related Papers (5)

Stereospecific Synthesis of Methyl Vinyl Ketones.

Addition of Grignard Reagents to Aryl Acid Chlorides: An Efficient Synthesis of Aryl Ketones.

One-Pot Sequential 1,2-Addition, Pd-Catalyzed Cross-Coupling of Organolithium Reagents with Weinreb Amides.

Effective Transformation of Unactivated Alkynes into Ketones or Acetals by Means of Au(III) Catalyst.

New Rhodium(II) Catalyzed Synthesis of 1,4-Dicarbonyl Compounds from α-Diazo Ketones Using Vinyl Ethers as Two-Carbon Synthons.