Memory of chirality in reactions involving monoradicals

Figures & data

Scheme 1. MoC in reaction involving fluorinated cyclopropyl radicals.

Scheme 2. MoC in decyanation reaction involving tetrahydropyranyl radicals (major reaction pathways depicted in black).

Scheme 3. Cyclization of a α-cyanotetrahydropyran derivative.

Scheme 4. MoC in the decarboxylation of a tetrahydropyran-2-carboxylic acid derivative (major reaction pathway depicted in black, k_H× [PhSH] > k_rac).

Scheme 5. MoC in a transannular cyclization.

Scheme 6. Cyclization of an axially chiral acrylamide.

Scheme 7. Cyclization of axially chiral N-allyl amide and carbamate.

Scheme 8. Phosphanylation reaction converting an axially chiral substrate to an axially chiral product.

Scheme 9. Radical addition–translocation–cyclization process.

Scheme 10. Radical translocation-cyclization.

Scheme 11. Unexpected formation of acetamides via a translocation-cyclization pathway.

Scheme 12. Heterofacial mechanism in a translocation–cyclization reaction.

Scheme 13. Radical amination of a benzylic C(sp³)–H bond.

Scheme 14. Reaction involving Cr(CO)₃-complexed benzylic radicals.

Scheme 15. The [3,2] allylperoxyl rearrangement.