A new two-step four-component synthesis of highly functionalized cyclohexenols by sequential nickel-catalyzed couplings.
A new two-step procedure for the synthesis of cyclohexenols has been developed. A nickel-catalyzed three-component addition of an enal, alkyne, and acetylenic tin affords substituted hept-4-en-6-ynals. The products of this first step then undergo a second nickel-catalyzed reaction with organozincs or organoboranes to afford densely functionalized cyclohexenols. Variation in each of the four components is tolerated to provide access to a wide range of versatile building blocks.
Lozanov
Mario
M
Department of Chemistry, Wayne State University, Detroit, Michigan 48202-3489, USA.
Montgomery
John
J
D002384:Catalysis; D003510:Cyclohexanes / Q000138:chemical synthesis*; D053138:Cyclohexenes; D000441:Hexanols / Q000138:chemical synthesis*; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry
D003510:Cyclohexanes; D053138:Cyclohexenes; D000441:Hexanols; D009942:Organometallic Compounds; C052568:cyclohexene; D009532:Nickel