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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Synthesis of new chiral bis(isoxazoline) ligands containing spiro[5.5]undecane skeleton
Midori A Arai1, Minori Kuraishi, Takayoshi Arai
1The Institute of Scientific and Industrial Research, Osaka University, Ibaraki, Osaka, Japan.
Abstract:
New chiral bis(isoxazoline) ligands bearing a spiro[5.5]undecane skeleton were designed and synthesized in five steps from diethyl malonate (3). These ligands showed a coordinating ability to Cu(II) as chiral ligands. A complex of (+)-(M*,S*,R*)-[5.5]-SPRIX 2b and Cu(OTf)(2) catalyzed the conjugate addition of diethyl-zinc to 2-cyclohexenone (8) to give (S)-3-ethyl-cyclohexanone (9) in 93% yield with 54% ee.
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