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Stereoselectivity In Amidyl Radical Cyclisations: Alkyl Mode Cyclisations

Andrew J. Clark,Robert J. Deeth,Christopher J. Samuel,Hathaichanuk Wongtap

SYNLETT（1999）

Cited 26|Views6
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Abstract
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.
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Key words
amidyl radicals, cyclisation, stereochemistry, hydroxamic acid derivatives, pyrrolidinones
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