Asymmetric addition of phenylzinc reagents to C-alkynyl nitrones. Enantiomeric enhancement by a product-like additive

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Asymmetric addition of diphenylzinc to C-alkynyl nitrones was achieved by utilizing di(t-butyl) (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active (S)-N-(1-phenyl-3-substituted prop-2-ynyl)hydroxylamines. By the addition of a product-like additive, enantiomeric enhancement was observed. A mixed zinc reagent, PhZnMe, improved the enantioselection to afford hydroxylamines in up to 92% ee. © 2008 Elsevier Ltd. All rights reserved.
2008-03-04