Synthesis of New Chiral Amines with a Cyclic 1,2-Diacetal Skeleton Derived from (2R, 3R)-(+)-Tartaric Acid

Molecules

M. Teresa Barros¹ 

关键词: Chiral amines;    1;    2-diacetals;    organocatalysts;    asymmetric Michael additions;    chiral ligands;   

DOI  :  10.3390/11020177

来源: mdpi

【 摘 要 】

The syntheses of new chiral cyclic 1,2-diacetals from (2R, 3R)-(+)-tartaric acid are described.  C₂-symmetrical diamines were prepared via direct amidation of the tartrate or from the corresponding bismesylate via reaction with sodium azide. For C₁-symmetrical compounds, the Appel reaction was used to form the key intermediate, a monochlorocarbinol, from the diol. Some of the new chiral compounds, produced in good to high yields, may be potentially useful as asymmetric organocatalysts or as nitrogen and sulfur chelating ligands for asymmetric metal catalyzed reactions. Thus, a bis-N-methyl-methanamine derivative, used in substoichiometric amounts, was found to catalyze the enantioselective addition of cyclohexanone to (E)-β-nitrostyrene with high diastereoselectivity (syn / anti = 92:8), albeit giving moderate optical purity (syn: 30 %).

【 授权许可】

Unknown   
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