Journal
ORGANIC LETTERS
Volume 9, Issue 16, Pages 3069-3072Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol071181d
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- NIGMS NIH HHS [R01 GM071779, R01GM071779, GM08496] Funding Source: Medline
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[GRAPHICS] 2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.
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