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Please login to access the full content or check if you have access via Variation 2: Cycloadditions and Miscellaneous Cyclizations

DOI: 10.1055/sos-SD-026-01067

Chataigner, I.; Harrison-Marchand, A.; Maddaluno, J.Science of Synthesis, (2005261180.

Not too many cycloaddition reactions give one-step access to oxo esters. Even if [4+2] cycloadditions between siloxy-substituted dienes [e.g., 2-(trimethylsiloxy)-1,3-dienes or Danishefsky's diene] and unsaturated esters and related functions (such as acrylates or maleic acid derivatives) could be considered as a general approach to the synthesis of oxo esters, they are not covered in this section because the ketone functionality is created during an independent hydrolysis step of the generally stable enol ether products. The hydrolysis of these products into ketones is detailed elsewhere in Science of Synthesis. The direct recovery of a ketone after cycloaddition requires the use of cumulenes such as ketenes (as the dienophiles) or vinylketenes (as dienes).

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