Organometallic reagents and protocols for synthesis

✍ Scribed by Alex G Fallis; Pat Forgione; Simon Woo; Stephanie Legoupy; Sandrine Py; Curtis Harwig; Tanya Rietveld

• Book ID: 104323679
• Publisher: Elsevier Science
• Year: 2000
• Tongue: English
• Weight: 97 KB
• Volume: 19
• Category: Article
• ISSN: 0277-5387
• DOI: 10.1016/s0277-5387(99)00402-7

✦ Synopsis

The addition of vinyl, aryl and alkynyl Grignard reagents to propargyl alcohols for the direct synthesis of dihydroxydienes (7), furans (9), butenolides (10) and enediyne alcohols (11) from a one-pot reaction involving a putative magnesium chelate intermediate (3) is described. Treatment of 5-bromo-1,3-pentadiene with indium metal in the presence of carbonyl compounds resulted in g-pentadienylation to generate 1,4-dienes (30). Dehydration afforded cross-conjugated trienes (31) for tandem Diels-Alder reactions, while the alcohol product (34) from an unsaturated aldehyde after oxy-Cope rearrangement afforded the 1,4-diene product (35) and ultimately hydrindane (36).