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20.6.1.6 Method 6: Mitsunobu Lactonization

DOI: 10.1055/sos-SD-020-01369

Maier, M. E.Science of Synthesis, (2007201475.

In the Mitsunobu reaction the adduct of triphenylphosphine and dialkyl azodicarboxylate causes activation of a hydroxy function via formation of an oxophosphonium intermediate 182 (Scheme 81). The activated hydroxy group can then be substituted with nucleophiles such as carboxylates.[‌247‌] With hydroxy acids 181, lactones 183 can be obtained. Some mechanistic studies have been reported.[‌248‌‌255‌]

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References


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