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A successful cycloaddition of solid supported diynes and carbodiimides was reported: Young, D. D.; Deiters, A. Angew. Chem., Int. Ed. 2007, 46, 5187.
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Other metal-catalyzed [2+2+2] cycloadditions involving isocyanates have been reported. Co: (a) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786.
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Ortho-substituted aryl alkynes are not tolerated under current conditions. Cycloaddition with 1-chloro-2-ethynylbenzene gives product 3 in only 35% yield and 31% ee, while 2-ethynyltoluene provides no cycloadduct.
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Ortho-substituted aryl alkynes are not tolerated under current conditions. Cycloaddition with 1-chloro-2-ethynylbenzene gives product 3 in only 35% yield and 31% ee, while 2-ethynyltoluene provides no cycloadduct.
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