A stereodivergent cascade imine → azomethine ylide → 1,3-dipolar cycloadditive approach to α-chiral pyrrolidines |
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Authors: | Philip Garner H Ümit Kaniskan |
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Institution: | Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, OH 44106-7078, USA |
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Abstract: | Stereodivergent 3+2] cycloadditions of chiral α-amino azomethine ylides leading to highly functionalized pyrrolidines are reported. The marriage of substrate conformational preferences and either an inter- or intramolecular cycloaddition manifold leads to either the l (syn) or u (anti) relationship between the pyrrolidine and α-stereocenters. The latter result may be applicable to a new approach to the bioxalomycin family of antibiotics. |
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Keywords: | Pyrrolidine synthesis Chiral azomethine ylides Stereocontrolled [3+2] cycloadditions |
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