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The Palladium–Catalyzed Cross-Coupling Reaction of Enol Acetates of α-Bromo Ketones with 1-Alkenyl-, Aryl-, or Alkylboron Compounds; A Facile Synthesis of Ketones and Their Enol Acetates

1992; Oxford University Press; Volume: 65; Issue: 10 Linguagem: Inglês

10.1246/bcsj.65.2863

1348-0634

Shigeru Abe, Norio Miyaura, Akira Suzuki,

Asymmetric Hydrogenation and Catalysis

Abstract The synthesis of stereodefined enol acetates of ketones is readily accomplished by palladium–catalyzed cross-coupling reaction between alkyl-, aryl-, or 1-alkylboron reagents with enol acetates of α-bromo ketones. Hydroboration of alkene with 9-BBN, followed by coupling with (Z)-2-ethoxy-1-bromoethene gives the enol ether of aldehyde. These enol acetates and ethers are readily deprotected to give corresponding ketones and aldehydes in high yields.