Stereoselective preparation of 1,4-dienes by palladium catalyzed allylation of (E)-alkenylpentafluorosilicates. Application to total synthesis of (±)-recifeiolide

✍ Scribed by Jun-ichi Yoshida; Kohei Tamao; Masatada Takahashi; Makoto Kumada

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 248 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)86834-9

✦ Synopsis

The formation of carbon-carbon bonds is one of the most fundamental problems in organic chemistry and numerous selective reactions have been explored by transition metal catalysis.2

We recently have shown that organopentafluorosilicates are potentially useful intermediates in organic synthesis for preparing carbon-halogen and -oxygen bonds.3 However, these compounds have scarcely been employed as effective reagents for the carbon-carbon bond formation.4

We have now found that alkenylpentafluorosilicates derived from terminal acetylenes readily react with allylic substrates under the influence of palladium salts to provide the cross-coupling product, 1,4-dienes, in good yields (Table 1).