BINOL-based azacrown ether catalyzed enantioselective Michael addition: asymmetric synthesis of a-aminophosphonates

publication · 11 years ago
by Truong Son Phama, János B. Czirok, Miklós Kubinyi, István Bitter, Krisztina Pál, Balázs László, Jászay Zsuzsa (Hungarian Academy of Sciences)
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Several novel 1,1′-bi-2-naphthyl-appended azacrown ethers with donor side-arms were synthesized and applied for the first time as chiral catalysts in the asymmetric Michael addition of an N-protected aminomethylenephosphonate onto acrylonitriles, resulting in high diastereoselectivity and enantioselectivity. The absolute configuration of the adduct was determined from its experimental and calculated CD spectra.
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