Elsevier

Tetrahedron Letters

Volume 38, Issue 35, 1 September 1997, Pages 6301-6304
Tetrahedron Letters

Cyclisation of Aminyl Radicals Derived from Amino Acids

https://doi.org/10.1016/S0040-4039(97)01413-5Get rights and content

Abstract

α-Amino acid aminyl radicals have been generated from sulfenamide precursors using Bu3SnH. The aminyl radicals undergo 5-exo-trig cyclisation reactions onto suitably placed N-alkenyl or α-alkenyl chains on the amino acids with reasonable diastereoselectivity. The α-ester of the amino acid imparts electrophilic behaviour to the aminyl radicals and facilitates cyclisation onto alkenes. © 1997 Elsevier Science Ltd.

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Acknowledgements

We thank Roche Discovery Welwyn and the EPSRC for a CASE Postgraduate Research Studentship (K.A.L.), the EPSRC for a research associate (D.R.C.) and for a 400 MHz NMR machine, and the EPSRC Mass Spectrometry Unit, Swansea University, Wales for mass spectra.

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