Stereospecific annulation of hydroxy vinyl ethers. Synthetic application to polyfunctionalized cyclic compounds

N Hanaki, K Ishihara, M Kaino, Y Naruse, H Yamamoto

Index: Hanaki, Naoyuki; Ishihara, Kazuaki; Kaino, Makoto; Naruse, Yuji; Yamamoto, Hisashi Tetrahedron, 1996 , vol. 52, # 21 p. 7297 - 7320

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Citation Number: 19

Abstract

Stereospecific annulation of hydroxy vinyl ethers in the presence of triflic anhydride and tertiary amines and its synthetic application are described. Each 1-hydroxy-2-oxabicyclo [n. 4.0] alkane, 2-oxabicyclo [n. 4.0] alk-1 (6)-ene and 2-oxabicyclo [n. 4.0] alk-1 (6+ n)-ene is stereoselectively synthesized from the same hydroxy vinyl ether depending on the choice of the reaction conditions (temperature, solvent and tertiaryamine). These compounds lead ...