Highly regio- and stereoselective four-component iodoamination of Se-substituted allenes. An efficient synthesis of N-(3-organoseleno-2-iodo-2(Z)-propenyl) acetamides |
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| Authors: | Ma Shengming Hao Xueshi Huang Xian |
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| Affiliation: | Department of Chemistry, Zhejiang University, Hangzhou 310028, PR China. masm@pub.sioc.ac.cn |
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| Abstract: | 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. |
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