Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www-thieme-connect-de.accesdistant.sorbonne-universite.fr/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2008(12): 1323-1323
DOI: 10.1055/s-0028-1083598
DOI: 10.1055/s-0028-1083598
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New YorkSn-Free Radical Addition of Acyloxymethyl to Imines
Contributor(s):Paul Knochel, Andreas J. WagnerK.-i. Yamada, M. Nakano, M. Maekawa, T. Akindele, K. Tomioka*
Kyoto University, Japan
Tin-Free Radical Addition of Acyloxymethyl to Imines
Org. Lett. 2008, 10: 3805-3808
Kyoto University, Japan
Tin-Free Radical Addition of Acyloxymethyl to Imines
Org. Lett. 2008, 10: 3805-3808
Further Information
Publication History
Publication Date:
20 November 2008 (online)
Key words
radical addition - imines - amino alcohols
Significance
Iodomethyl esters were converted into the corresponding acyloxymethyl radicals and successfully underwent addition to the C=N bond of various protected imines. The resulting aminoethyl esters are then readily cleaved by KOH yielding N,2-disubstituted 2-aminoethanol derivatives.
Comment
Acyloxymethyl iodides constitute useful synthetic equivalents for the hydroxymethyl anion thanks to the easy deprotection of the alcohol moiety under standard basic conditions. Moreover, no tin compounds are required and the reaction takes place under ordinary atmosphere and at room temperature, which makes this reaction very appealing.