An Intramolecular Prins Double Cyclization Catalyzed by Silyl Triflates1

ME Jung, S Angelica, DC D'Amico

Index: Jung, Michael E.; Angelica, Steve; D'Amico, Derin C. Journal of Organic Chemistry, 1997 ,  vol. 62,  # 26  p. 9182 - 9187

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Citation Number: 10

Abstract

Several intramolecular Prins double cyclizations are reported. The 2-alkyl 5-hepten-1, 2- diols and their analogues, 9-11, were prepared and oxidized to the aldehydes 6-8 under Swern conditions. Treatment of these α-hydroxy aldehydes with TBSOTf and a hindered base gave the products of an intramolecular Prins double cyclization, namely the 7-(silyloxy)- 2-oxabicyclo [2.2. 1] heptanes, 17-19, in 84-92% yield. These compounds were formed as ...