Regioselective hydronickelation of allenes and its application to the hydrocyanative carbocyclization reaction of allene-ynes and bis-allenes.
The carbocyanative cyclization of allene-ynes and bis-allenes under nickel catalysis is described. The key steps are the regioselective hydronickelation of allenes and subsequent cyclization via carbometalation. The former step determines the reaction pathway, and the latter controls the stereochemistry of substituted olefins. The products are useful carbo- and heterocycles that include a cyano group, functionalized double bonds, and quaternary carbons.
Graduate School of Pharmaceutical Sciences, Chiba University 1-8-1 Inohana, Chuo-ku, Chiba, Japan 260-8675.
Yuka
Y
Amako
Hiroto
H
Hori
Shigeru
S
Arai
Atsushi
A
Nishida
D000466:Alkadienes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
D000466:Alkadienes; D000475:Alkenes; D010165:Palladium; D009532:Nickel