Stereoselectivity in amidyl radical cyclisations. Acyl mode cyclisations
1998; Elsevier BV; Volume: 39; Issue: 33 Linguagem: Inglês
10.1016/s0040-4039(98)01189-7
ISSN1873-3581
AutoresAndrew J. Clark, Joanne L. Peacock,
Tópico(s)Organic and Inorganic Chemical Reactions
ResumoAmidyl radicals generated from tributylstannane mediated homolysis of O-benzoyl hydroxamic acid derivatives undergo 5-exo cyclisation to give mixtures of cis and trans pyrrolidinones. While the steric nature of the nitrogen substituents investigated had little effect on the diastereoselectivity of the process they did effect the relative rate of the cyclisation reactions. The major products could be predicted by application of the “Beckwith rule”.
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