γ-Heteroatom directed stereocontrolled Staudinger cycloaddition reaction of vinylketenes and imines |
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| Authors: | Aarif L Shaikh ARAS Deshmukh |
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| Institution: | a Division of Organic Chemistry (Synthesis), National Chemical Laboratory, Pune 411 008, India
b Center for Materials and Characterization, National Chemical Laboratory, Pune 411 008, India |
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| Abstract: | Vinylketenes possessing a γ-heteroatom, on Staudinger cycloaddition reaction with imines gave trans-3-vinyl-β-lactams in very good yields. The vinyl side chain stereoselectively adopts the Z-configuration in the transition state to stabilize the vinylketene and produces, exclusively, trans-3-vinyl-β-lactams. |
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| Keywords: | Staudinger reaction Stereoselective synthesis Vinylketenes Imines |
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