title: A highly stereoselective addition of lithiated ynamides to Ellman-Davis chiral N-tert-butanesulfinyl imines.
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.
authors: Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin , Madison, Wisconsin 53705, United States.
authors: Xiao-Na
authors: XN
authors: Wang
authors: Richard P
authors: RP
authors: Hsung
authors: Rui
authors: R
authors: Qi
authors: Sierra K
authors: SK
authors: Fox
authors: Ming-Can
authors: MC
authors: Lv
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000577:Amides / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D023303:Oxazolidinones / Q000737:chemistry*; D013237:Stereoisomerism; D013452:Sulfonium Compounds / Q000737:chemistry*
chemical_list: D000480:Alkynes; D000577:Amides; C481933:N-tert-butanesulfinylimino ester; D023303:Oxazolidinones; D013452:Sulfonium Compounds
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