New Synthetic Developments

Part of the Reactivity and Structure Concepts in Organic Chemistry book series (REACTIVITY, volume 26)


Lee and Richardson have disclosed that it is entirely feasible to cyclopentannulate silyl enol ethers in a one-pot two-step process. For example, condensation of 1 with the readily available stannane 2 in the presence of trimethylsilyl triflate leads to an adduct that cyclizes to 3 on subsequent exposure to titanium tetrachloride [5]. This new strategy is notable in that a doubly functionalized product results. 1,2-Bis(trimethylsilyloxy)cyclopentene (4) condenses with chloride 5 in the presence of anhydrous zinc chloride to give a 1:1 mixture of 6 and 7 [6]. The first relevant point is that alkylation proceeds without annihilation of the allylsilane moiety. Consequently, this functionality is available for subsequent ring closure as illustrated by the independent conversion of 6 and 7 to 8 and 9, respectively, when treated with ethylaluminum dichloride.


Ring Expansion Diazo Ketone Synthetic Development Anhydrous Zinc Chloride Silyl Enol Ether 
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Copyright information

© Springer-Verlag Berlin Heidelberg 1987

Authors and Affiliations

  1. 1.Evans Chemical LaboratoriesThe Ohio State UniversityColumbusUSA

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