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Enantioselective Synthesis of Quaternary α‑Amino Acids via l-tert-Leucine-Derived Squaramide-Catalyzed Conjugate Addition of α‑Nitrocarboxylates to Enones

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journal contribution
posted on 31.05.2016, 00:00 by Kalisankar Bera, Nishikant S. Satam, Irishi N. N. Namboothiri
Enantioselective Michael addition of tertiary α-nitroesters to β-unsubstituted vinyl ketones has been carried out in the presence of an l-tert-leucine-derived squaramide as organocatalyst. The products, quaternary α-nitroesters, were formed in excellent yield and moderate to good ee’s in most cases. Scale-up of the reaction and synthetic applications of the products, including transformation to representative quaternary α-amino acids, have also been demonstrated.