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Intramolecular cyclopropanation followed by ring opening of remotely placed furan was demonstrated using rhodium(II) catalysed cyclic diazoamides tethered on furan to produce 12- to 23-membered oxindole incorporated macrocycles. The length of the spacer is an important factor to decide the stereoselectivity of the product.
Reaction of cyclic diazoamides and cyclic olefins or heteroaromatic systems using copper(I) triflate as a catalyst furnished a variety of strained spiro-cyclopropanooxindoles in a diastereoselective manner under mild reaction conditions. The effect of copper(I) triflate and rhodium(II) acetate catalysts on the cyclopropanation was also studied.
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