Diastereomeric control of photoinduced Diels–Alder reactions of 1-anthracen-9-yl-ethanol by hydrogen-bonding effects

✍ Scribed by J.C.Christian Atherton; Simon Jones

• Book ID: 104231790
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 90 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01742-7

✦ Synopsis

Photoinduced Diels-Alder reactions of 1-anthracen-9-yl-ethanol with maleic anhydride proceed with high diastereoselection but with complete reversal of the sense of selectivity compared to analogous O-methyl compound. Hydrogen-bonding effects have been established as the predominant factors in determining this selectivity.