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7.1.5.3.5 Variation 5: Transformation of Esters

DOI: 10.1055/sos-SD-007-00142

Ooi, T.; Maruoka, K.Science of Synthesis, (20047204.

The reaction of esters with dialkylaluminum alkanethiolates leads to the formation of thioesters, offering a uniquely simple procedure for the generation of these compounds (Scheme 16).[‌19‌‌21‌] This method is particularly effective for the facile preparation of tert-butyl thioesters from the corresponding methyl and ethyl esters.[‌22‌] However, the reaction with α,β-unsaturated esters generally gives conjugate addition products.

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