Stereoselective aldol condensation reactions of iron acetyl enolates

✍ Scribed by Lanny S. Liebeskind; Mark E. Welker

• Book ID: 104233800
• Publisher: Elsevier Science
• Year: 1984
• Tongue: French
• Weight: 237 KB
• Volume: 25
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)81433-7

✦ Synopsis

By proper choice of counterion, the enolate of n5-CpFe(CO)(PPh3)COCH3 will react with aldehydes to form the aldol products with high stereoselectivity. Chiral iron acyls, n5-CpFe(CO)(PPh3)COCH2R, can be deprotonated by strong base to the corresponding enolates that then react with organic electrophiles (RX, RCHO, RCH=NR') to produce new, elaborated iron acyls. 2-7 Mild oxidative cleavage of these iron acyls proceeds in high yield to organic acid derivatives thus making these iron complexes chiral enolate equivalents.