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Stereoselectivity in amidyl radical cyclisations. Acyl mode cyclisations

โœ Scribed by Andrew J Clark; Joanne L Peacock

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
185 KB
Volume
39
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Amidyl 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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