Nickel-Catalyzed Chemo- and Enantioselective Coupling between Cyclobutanones and Allenes: Rapid Synthesis of [3.2.2] Bicycles.
Herein an intramolecular nickel-catalyzed (4+2) coupling between cyclobutanones and allenes, by C-C cleavage, is reported. The reaction provides a distinct approach for accessing [3.2.2] bicyclic scaffolds which are challenging to prepare through conventional approaches. The reaction is efficient, chemoselective, and pH/redox neutral. Room temperature conditions and low catalyst loadings can be adopted. Excellent enantioselectivity is also achieved.
Department of Chemistry, University of Texas at Austin, Austin, TX, 78712, USA.|Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA.
Xuan
X
Zhou
Department of Chemistry, University of Texas at Austin, Austin, TX, 78712, USA.|Department of Chemistry, University of Chicago, Chicago, IL, 60637, USA.
Guangbin
0000-0003-1331-6015
G
Dong
D000466:Alkadienes / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003503:Cyclobutanes / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000466:Alkadienes; D001643:Bridged Bicyclo Compounds; D003503:Cyclobutanes; D009942:Organometallic Compounds; D009532:Nickel
C−C activation; allenes; cycloaddition; nickel; small ring systems