Cyclobutyl phenyl sulfoxide and (SR)-cyclobutyl p-tolyl sulfoxide: New reagents for the spiroannelation of cyclopentanone
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Add time:09/10/2019 Source:sciencedirect.com
Cyclobutyl phenyl sulfide 2, cyclobutyl phenyl sulfoxide 3 and (SR)-cyclobutyl p-tolyl sulfoxide (SR)-8 have been synthesized and used for the spiroannelation of cyclopentanone. In the most effective sequence, lithiated 3 is added to ketones with formation of β-hydroxy sulfoxides 4a-g, which are ring enlarged and hydrolyzed to cyclopentanones 6a-e and sulfanylcyclopentene 6f, respectively, after reduction to β-hydroxy sulfides 5a-f. In an asymmetric version using (SR)-8, partial racemization during ring enlargement was observed.
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