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Halo- and Cyano-Sulfonylation of BCB-Tethered Allyl Amides via Photoredox-Catalyzed Radical-Polar Crossover
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J
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L
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J
DOI：10.1021/acs.joc.6c00608.png)
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Abstract
En 中文
A photoredox-catalyzed halo- and cyano-sulfonylation of BCB-tethered allyl amides with sulfonyl chlorides (or TsCN) as bifunctional reagents is reported, enabling the synthesis of functionalized spirocyclobutyl lactams containing multiple stereocenters. This transformation involves a sequential radical addition/5-exo-trig cyclization/radical-polar crossover cascade that proceeds across the strained C-C bond of the BCBs and a C=C bond. Notable features of this approach include the formation of three new chemical bonds in a single step, complete atom economy, and the versatile derivatization of the products.
Keywords:
photoredox catalysis
radical-polar crossover
sulfonyl chlorides
spirocyclobutyl lactams
stereocenters
Journal
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3.6
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5.4W
Citations:
8.8W
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Cited Papers