The Journal of Organic Chemistry

[3+ 4] and [3+ 5] Annulation Reactions of. alpha.-(Phenylthio) Dicarbonyl Electrophiles with Bis (trimethylsilyl) Enol Ethers: Synthesis of Highly Functionalized Medium …

GA Molander, PR Eastwood

Index: Molander, Gary A.; Eastwood, Paul R. Journal of Organic Chemistry, 1995 , vol. 60, # 26 p. 8382 - 8393

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Citation Number: 26

Abstract

The [3+ 41 and [3+ 51 annulations of bis (trimethylsily1) enol ethers with 1, 4-and 1, 5- dicarbonyl electrophiles bearing a-phenylthio substituents leads to the formation of bicyclic 13.2. 11 and [3.3. 11 ethers with good regiochemical and stereochemical control. Subsequent oxidation of the phenylthio moiety followed by reduction with SmIz constitutes a high-yielding and regioselective process for cleavage of the bridging ether linkage. The ...