Aldol condensation with (phenylseleno)acetaldehyde and radical cyclization leads to cis-fused bicyclic compounds when applied (Scheme 1) to esters of cycloalk-2-enylacetic acid; trans-isomers are formed when the reactions are used (Scheme 2) in conjunction with organocuprate-mediated addition to cycloalkenones.
D. L. J. Clive, D. R. Cheshire and L. Set, J. Chem. Soc., Chem. Commun., 1987, 353 DOI: 10.1039/C39870000353
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