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Synthesis of Cyclohexenols and Cycloheptenols via the Regioselective Reductive Ring Opening of Oxabicyclic Compounds

โœ Scribed by Lautens, Mark; Ma, Shihong; Chiu, Pauline


Book ID
127114289
Publisher
American Chemical Society
Year
1997
Tongue
English
Weight
502 KB
Volume
119
Category
Article
ISSN
0002-7863

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โœ Mark Lautens; Tomislav Rovis ๐Ÿ“‚ Article ๐Ÿ“… 1998 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 531 KB

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