Synthesis of Oxacycles by Tandem Radical Addition− Cyclization Reactions

MP Sibi, K Patil, TR Rheault

Index: Sibi, Mukund P.; Patil, Kalyani; Rheault, Tara R. European Journal of Organic Chemistry, 2004 , # 2 p. 372 - 384

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Citation Number: 10

Abstract

Abstract β-Alkoxyalkylidenemalonates undergo tandem radical addition− cyclization reactions to provide oxacycles of different ring sizes in good chemical efficiency. A variety of nucleophilic radicals participate in the addition− cyclization reactions, and the reaction requires the use of lanthanide triflates as Lewis acids. Compound 9 gave the 5-exo cyclization product 13 in 80% yield and greater than 50: 1 diastereoselectivity favoring the ...