ChemInform Abstract: Chelation-Assisted Intermolecular Hydroacylation: Direct Synthesis of Ketone from Aldehyde and 1-Alkene.

✍ Scribed by C.-H. JUN; H. LEE; J.-B. HONG

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199726091

✦ Synopsis

The work describes a general direct intermolecular hydroacylation -not reported so far -of 1-alkene with aldehyde using the cocatalyst system of the transition metal complex and 2-amino-3-picoline. Some other metal complexes are also catalytically active. Without the addition of the picoline derivative, the decarbonylation product anisole is obtained exclusively in 46% yield, e.g., from the reaction of (Ia) and (II). This result indicates that hydroacylation competes with the decarbonylation of the aldehyde. In the reaction of a chiral olefin such as (Ie) with (II), the resulting ketone (IIIe) retains an asym. center in the 3-cyclohexenyl group. Aliphatic and aromatic aldehydes show comparable activity. The reaction of a sterically hindered aliphatic aldehyde, e.g. (IVe) affords a low yield of ketone ( Ve) compared with those of prim. and sec.