- Visible-Light-Induced Cycloaddition of α-Ketoacylsilanes with Imines: Facile Access to β-Lactams
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We report the synthesis of β-lactams from α-ketoacylsilanes and imines, which proceeds via a formal [2+2] photochemical cycloaddition with in situ generation of siloxyketene. This mild and operationally simple reaction proceeds in an atom-economic fashion with broad substrate scope, including aldimines, ketimines, hydrazones, and fused nitrogen heterocycles, affording a variety of important β-lactams with satisfactory diastereoselectivities in most cases. This reaction also features good functional-group tolerance, facile scalability and product diversification. Experimental and computational studies suggest that α-ketoacylsilanes can serve as photochemical precursors by engaging in a 1,3 silicon shift to the distal carbonyl group.
- Ye, Jian-Heng,Bellotti, Peter,Paulisch, Tiffany O.,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 13671 - 13676
(2021/05/11)
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- Synthesis of β-lactams via cycloaddition of hydrazones with phenoxyketene
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Phenoxyketene is capable of annelating the disubstituted hydrazones to afford stereoselectivity cis-monocyclic β-lactams with a 1-amino functionality. The ease of cycloaddition is governed by substitutents on the azomethine carbon as well as on the hydraz
- Sharma,Pandhi
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p. 2196 - 2200
(2007/10/02)
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