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  • Title: Enantioselective Polyene Cyclization Catalyzed by a Chiral Brønsted Acid.
    Author: Fan L, Han C, Li X, Yao J, Wang Z, Yao C, Chen W, Wang T, Zhao J.
    Journal: Angew Chem Int Ed Engl; 2018 Feb 19; 57(8):2115-2119. PubMed ID: 29316110.
    Abstract:
    The first enantioselective polyene cyclization initiated by a BINOL-derived chiral N-phosphoramide (NPA) catalyzed protonation of an imine is described. The ion-pair formed between the iminium ion and chiral counter anion of the NPA plays an important role for controlling the stereochemistry of the overall transformation. This strategy offers a highly efficient approach to fused tricyclic frameworks containing three contiguous stereocenters, which are widely found in natural products. In addition, the first catalytic asymmetric total synthesis of (-)-ferruginol was accomplished with an NPA catalyzed enantioselective polyene cyclization, as the key step for the construction of the tricyclic core, with excellent yield and enantioselectivity.
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