Abstract
A new domino reaction is developed for the synthesis of optically active 3-pyrrolines. The reaction involves the use of (trimethylsilyl)aryl triflates, KF, Schiff bases, and alkynes in the presence of a chiral catalyst (R)-(–)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate. The key features of this reaction include the generation of a single product in very good yields with high stereo- and enantioselectivity. The enantiomeric ratio reaches as high as 98.5:1.5. The overall pathway includes four steps in a domino process of 1,2-elimination, 1,2-nucleophilic addition, 1,4-proton shift, and (3+2) cycloaddition. More information can be found in the Full Paper by Jih Ru Hwu et al.
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