Highly regio- and stereoselective four-component iodoamination of Se-substituted allenes. an efficient synthesis of N-(3organoseleno-2-iodo-2(Z)-propenyl) acetamides

Z-Selectivity was observed for iodohydroxylation of Se-substituted allenes with I2 and H2O, which is opposite to that of 1,2-allenyl sulfoxides. With n-hexane as the co-solvent Z-iodoamination leading to N-(3-organoseleno-2-iodo-2(Z)-propenyl)acetamide was observed. A brief rational for the stereoselectivity of this reaction is provided.