Intramolecular aminyl and iminyl radical additions to alpha,beta-unsaturated esters. Diastereoselective tandem cyclofunctionalization and hydrogen transfer reactions.
[reaction: see text] A tandem process featuring intramolecular aminyl radical cyclofunctionalization and hydrogen transfer affords 2,3-trans-disubstituted pyrrolidines with anti or syn diastereoselectivity. The extension of this strategy to iminyl radicals gives trans-anti pyrrolenines with high levels of 1,2-induction in both steps of the tandem process.
Guindon
Y
Y
Institut de recherches cliniques de Montréal (IRCM), Bio-organic Chemistry Laboratory, 110, avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7. guindoy@ircm.qc.ca
Guérin
B
B
Landry
S R
SR