Synthesis of spiroacetals using functionalised titanium carbenoids |
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| Authors: | Calver A Main Richard C Hartley |
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| Institution: | a WestChem, Department of Chemistry, The Joseph Black Building, University of Glasgow, Glasgow G12 8QQ, UK
b GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex, CM19 5AW, UK |
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| Abstract: | Alkylidenation of lactones with functionalised titanium carbenoid reagents (Schrock carbenes) followed by acid-induced cyclisation of the resulting enol ethers constitutes a new method for the preparation of 4.4], 4.5] and 5.5] spiroacetals (1,6-dioxaspiro4.4]nonanes, 1,6-dioxaspiro4.5]decanes and 1,7-dioxaspiro5.5]undecanes, respectively, sometimes termed 5,5-, 5,6- and 6,6-spiroketals). The titanium carbenoids are easily generated from readily available thioacetals. |
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| Keywords: | Spiroketal Spiroacetal Lactone Titanium Schrock carbene Thioacetal |
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