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Synlett 1999; 1999(4): 444-446
DOI: 10.1055/s-1999-2640
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Stereoselectivity in Amidyl Radical Cyclisations: Alkyl Mode Cyclisations

Andrew J. Clark* , Robert J. Deeth, Christopher J. Samuel, Hathaichanuk Wongtap
  • *Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK; Fax +44(12 03)52 41 12; E-mail: msrir@csv.warwick.ac.uk
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Publication Date:
31 December 1999 (online)

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Amidyl radicals 2 generated from tributylstannane mediated homolysis of O-benzoyl hydroxamic acid derivatives 6a-g undergo alkyl mode 5-exo cyclisation to give mixtures of cis and trans N-acyl pyrrolidinones (d.e. = 54-74%). The efficiency of the process was found to be dependant upon the steric and electronic nature of the nitrogen substituent.

amidyl radicals - cyclisation - stereochemistry - hydroxamic acid derivatives - pyrrolidinones