Issue 9, 2003

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
22 Jan 2003
Accepted
27 Feb 2003
First published
02 Apr 2003

Chem. Commun., 2003, 1082-1083

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

S. Ma, X. Hao and X. Huang, Chem. Commun., 2003, 1082 DOI: 10.1039/B300879G

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