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  • Title: Relaying asymmetry of transient atropisomers of o-iodoanilides by radical cyclizations.
    Author: Petit M, Lapierre AJ, Curran DP.
    Journal: J Am Chem Soc; 2005 Nov 02; 127(43):14994-5. PubMed ID: 16248616.
    Abstract:
    Atropisomers of N-2 degrees -alkyl-N-acryloyl-2-iodoanlides have been resolved by chromatography and crystallization-induced asymmetric transformation. These molecules have atropisomerization barriers of 23-24 kcal/mol and return to equilibrium ratios over several hours at ambient temperature in solution. The transient chirality can be locked in by radical cyclizations, which provide N-2 degrees -alkyl-3-methyl-1,3-dihydroindol-2-ones with high levels of chirality transfer. The mechanistic model features a stereoselective aryl radical cyclization that is more rapid than the rotation of the N-aryl bond of the anilide.
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