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One-pot protocol to functionalized benzopyrrolizidine catalyzed successively by Rh2(OAc)4 and Cu(OTf)2: a transition metal-Lewis acid catalysis relay.

One-pot protocol to functionalized benzopyrrolizidine catalyzed successively by Rh2(OAc)4 and Cu(OTf)2: a transition metal-Lewis acid catalysis relay.

Organic letters (2014-12-17)

Hua-Dong Xu, Zhi-Hong Jia, Ke Xu, Hao Zhou, Mei-Hua Shen

摘要

4-N-allylarylpropylamino-1-sulfonyl triazoles are converted to structurally unique benzopyrrolizidinyl sulfonamides in a one-pot operation. Intramolecular capture of rhodium carbene with arylamino nitrogen gives rise to the formation of an ammonium ylide immediate. A [2,3]- or [1,2]-rearrangement occurs to give a 2-allylpyrrolidinyl-2-carbimine intermediate which undergoes Cu(OTf)2 catalyzed aza-Friedel-Crafts cyclization to finish a highly functionalized tricyclic system decorated with a synthetically difficult quaternary carbon center, a sulfonamide group, and an allyl segment.

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三氟甲磺酸锌, 98%

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三氟甲磺酸, ReagentPlus^®, ≥99%

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三氟甲烷磺酸银, ≥99%

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三氟甲磺酸, reagent grade, 98%

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三氟甲磺酸铝, 99.9% trace metals basis

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二聚醋酸铑, ≥97%, powder

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三氟甲磺酸锂, 99.995% trace metals basis

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三氟甲烷磺酸银, ≥99.95% trace metals basis

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三氟甲磺酸镧(III), 99.999% trace metals basis

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二聚醋酸铑, 99.9% trace metals basis

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三氟甲磺酸锂, 96%

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铑, powder, 99.95% trace metals basis

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三氟甲烷磺酸银, purum, ≥98.0% (Ag)

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三氟甲磺酸钡, 98%

铑, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%

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铑, wire reel, 0.05m, diameter 0.12mm, as drawn, 99.9%

铑, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 99.9%

铑, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.9%