Stereoselective syntheses of. ALPHA.-substituted cyclic ethers and syn-1, 3-diols.

K Homma, H Takenoshita, T Mukaiyama

Index: Homma, Koichi; Takenoshita, Haruhiro; Mukaiyama, Teruaki Bulletin of the Chemical Society of Japan, 1990 , vol. 63, # 7 p. 1898 - 1915

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Citation Number: 28

Abstract

In the presence of a catalytic amount of triphenylmethylium hexachloroantimonate or a catalyst system of antimony pentachloride, chlorotrimethylsilane and tin (II) iodide, α- substituted cyclic ethers are stereoselectively prepared from lactones by successive treatment with 1-(t-butyldimethylsiloxy)-1-ethoxyethene and silyl nucleophiles such as triethylsilane, allyltrimethylsilane and trimethylsilyl cyanide. These catalysts also promote ...