Scope of the nickel catalyzed asymmetric reductive ring opening reaction. Synthesis of enantiomerically enriched cyclohexenols

✍ Scribed by Mark Lautens; Tomislav Rovis

• Book ID: 104208243
• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 531 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)10211-3

✦ Synopsis

Subjecting a variety of oxabicyclo[2.2.1lheptenes to diisobutylaluminum hydride (DIBAL-H) in the presence of a catalytic amount of Ni(COD) 2 and (R)-BINAP results in a highly enantioselective ring opening to generate cyciohexenois with ee's typically greater than 90%. The scope of this reaction has been delineated and alternative nickel catalysts have been examined which are less sensitive than Ni(COD)2.