Journal
ORGANIC LETTERS
Volume 13, Issue 16, Pages 4180-4183Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol201486x
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- Natural Sciences and Engineering Research Council of Canada
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The reaction of cyclopropanes, geminally disubstituted with one carboalkoxy and one carbohydroxy group, undergoes ring-opening reactions with indole nucleophiles under catalyst-free, hyperbaric (13 kbar) conditions. An internal hydrogen bond is postulated as the mode of activation obviating the need for the Lewis acid catalyst normally used for such donor-acceptor cyclopropane chemistry. These conditions avoid decarboxylation and yield useful adducts with the carboxylic acid group Intact for further elaboration.
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