Highly regio- and stereoselective four-component iodoamination of Se-substituted allenes. An efficient synthesis of N-(3-organoseleno-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.
Ma
Shengming
S
Department of Chemistry, Zhejiang University, Hangzhou 310028, PR China. masm@pub.sioc.ac.cn
Hao
Xueshi
X
Huang
Xian
X