The Journal of Organic Chemistry

Ring-Enlarging Annulations. A One-Step Conversion of Cyclic Silyl Acyloins and. omega.-Alkynyl Acetals to Polycyclic Enediones

A Balog, DP Curran

Index: Balog, Aaron; Curran, Dennis P. Journal of Organic Chemistry, 1995 , vol. 60, # 2 p. 337 - 344

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Citation Number: 40

Abstract

A new sequence of cationic reactions that converts cyclic silyl acyloins and w-alkynyl acetals to polycyclic enediones is reported. For example, treatment of bis-1, 2-((trimethylsilyl) oxy) cyclobutene and 2-(ethylenedioxy)-5-heptyne with excess boron trifluoride etherate in methylene chloride for 2 days provides 4-acetyl-3, 5, 6, 6a-tetrahydro-6a-methyl-l-(fZH)- pentalenone in 58% yield.“his product is formed via a sequence involving a Mukaiyama ...