- 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
PMID25496025
ABSTRACT
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.
MATERIALS
Product Number
Brand
Product Description
Rhodium, wire reel, 0.1m, diameter 1.0mm, as drawn, 99.9%
Rhodium, wire reel, 0.05m, diameter 0.12mm, as drawn, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, x-ray quality, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.2m, diameter 0.25mm, hard, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.05m, diameter 0.5mm, as drawn, 99.9%
Rhodium, microfoil, disks, 10mm, thinness 0.50μm, specific density 620μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, wire reel, 0.2m, diameter 0.12mm, as drawn, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 25x25mm, thickness 0.006mm, as rolled, 99.9%
Rhodium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.9%
Rhodium, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.9%
Rhodium, foil, 25x25mm, thickness 0.125mm, as rolled, 99.9%
Rhodium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%
Rhodium, foil, not light tested, 10x10mm, thickness 0.012mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.0005mm, permanent polyester support, 99.85%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 99.9%
Rhodium, wire reel, 0.5m, diameter 0.12mm, as drawn, 99.9%
Rhodium, microfoil, disks, 10mm, thinness 0.1μm, specific density 124μg/cm2, permanent mylar 3.5μm support, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.00025mm, permanent polyester support, 99.9%