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Two different enantioselective organocatalytic cascade reactions to form new sulfur-containing spirocyclic scaffolds are described. In the first approach, benzothiophen-2-one and enals react in the presence of a secondary amine catalyst through a Michael/Michael/Aldol sequence to afford the final spiro-cyclohexene carbaldehydes in good yields (up to 68 %) and with excellent selectivities [20:1 diastereomeric ratio (dr), up to 99 % ee]. In the second approach, the double Michael addition of benzothiophen-2-one to aromatic dienones with primary amine catalysis produces the corresponding spiro-cyclohexanones in good yields (up to 76 %) and with moderate-to-high selectivities (up to 12:1 dr, up to 90 % ee). Moreover, the use of N-phenylrhodanine as the bis-nucleophile for these reactions also allowed the formation of the corresponding spirocyclic adducts. Benzothiophenone and N-phenylrhodanine were successfully used as bis-nucleophiles in two enantioselective organocatalytic cascades. Their reactions with enals and dienones allowed the formation of new sulfur-containing spirocyclic scaffolds in good yields and with high selectivities. Copyright
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Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate