Journal
ORGANIC LETTERS
Volume 19, Issue 2, Pages 372-375Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b03573
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- CSIR [CSC0108]
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The possibility of fluoride-mediated selective dephosphonylation of alpha-diazo-beta-carbonyl phosphonates such as the Ohira-Bestmann reagent has been proposed and executed. The resulting alpha-diazocarbonyl intermediates undergo a (3 + 2)pcycloaddition at room temperature with conjugated olefins and benzynes. Interestingly, under the current conditions, the resulting cycloaddition products underwent either N-acylation (with excess alpha-diazo-beta-carbonyl phosphonates) or Michael addition (with conjugated olefins).
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