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Domino reactions of rhodium(II) carbenoids for alkaloid synthesis.

Chemical Society reviews (2009-10-23)
Albert Padwa
ABSTRACT

In this tutorial review, the rhodium(II)-catalyzed domino reactions of alpha-diazo carbonyl compounds are summarized. The article will emphasize some of the more recent synthetic applications of the rhodium carbenoid cyclization/cycloaddition domino cascade for alkaloid synthesis. The many structurally diverse and highly successful examples of both oxa and azapolycyclic ring formation cited in this tutorial review clearly demonstrate that the domino cyclization/cycloaddition cascade of metallo carbenoids has evolved as an important strategy for the synthesis of nitrogen containing natural products.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Rhodium, powder, 99.95% trace metals basis
Rhodium, foil, not light tested, 25x25mm, thickness 0.0005mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.1m, diameter 1.0mm, 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 0.00075mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.1m, diameter 0.5mm, as drawn, 99.9%
Rhodium, wire reel, 0.5m, diameter 0.25mm, hard, 99.9%
Rhodium, foil, 25x25mm, thickness 0.1mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, microfoil, disks, 10mm, thinness 0.50μm, specific density 620μg/cm2, permanent mylar 3.5μm support, 99.99%
Rhodium, foil, light tested, 15x15mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.006mm, as rolled, 99.9%
Rhodium, microfoil, disks, 25mm, thinness 0.1μm, specific density 124μg/cm2, permanent mylar 3.5μm support, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.012mm, as rolled, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.05mm, as rolled, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00025mm, permanent polyester support, 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, wire reel, 0.05m, diameter 0.25mm, hard, 99.9%
Rhodium, foil, 25x25mm, thickness 0.125mm, as rolled, 99.9%
Rhodium, wire reel, 0.05m, diameter 0.5mm, as drawn, 99.9%
Rhodium, foil, not light tested, 10x10mm, thickness 0.012mm, as rolled, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.001mm, permanent polyester support, 99.85%
Rhodium, foil, 25x25mm, thickness 0.15mm, as rolled, 99.9%
Rhodium, foil, not light tested, 25x25mm, thickness 0.00025mm, permanent polyester support, 99.9%
Rhodium, foil, light tested, 25x25mm, thickness 0.075mm, as rolled, 99.9%
Rhodium, foil, not light tested, 50x50mm, thickness 0.00075mm, permanent polyester support, 99.85%
Rhodium, wire reel, 0.2m, diameter 0.5mm, as drawn, 99.9%
Rhodium, wire reel, 0.05m, diameter 1.0mm, as drawn, 99.9%
Rhodium, wire reel, 0.1m, diameter 0.25mm, hard, 99.9%