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  • Title: A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.
    Author: Wang XN, Hsung RP, Qi R, Fox SK, Lv MC.
    Journal: Org Lett; 2013 May 17; 15(10):2514-7. PubMed ID: 23646900.
    Abstract:
    A highly diastereoselective addition of lithiated ynamides to Ellman-Davis chiral imines is described. While additions of N-sulfonyl ynamides are highly stereoselective even without Lewis acids, the use of BF3-OEt2 completely reversed the stereoselectivity. In addition, oxazolidinone-substituted ynamides behaved differently and functioned better with BF3-OEt2, and the chirality of the oxazolidinone ring exerts no impact on the selectivity.
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