Memory of chirality in reactions involving monoradicals.
The effects of memory of chirality (MoC) in reactions involving monoradical species are reviewed here. Reactions involving a nonracemic chiral starting material bearing a single stereogenic element such as a chiral center or chiral axis directly involved in the new bond formation are discussed. These reactions lead to a nonracemic product via an intermediate susceptible to rapid racemization. Memory of chirality has been observed in cyclic radicals, aryl, ester/amide substituted acyclic radicals, and benzylic radicals at temperatures up to 130 °C.
a Department of Chemistry and Biochemistry , University of Bern , Bern , Switzerland.
Christian Simon
CS
Gloor
b Universite de Nantes, UFR Science et Techniques - UMR CNRS 6230 , 2 rue de la Houssinière , Nantes , France.
Fabrice
F
Dénès
a Department of Chemistry and Biochemistry , University of Bern , Bern , Switzerland.
Philippe
P
Renaud
D046528:Chimerism; D005609:Free Radicals; D015394:Molecular Structure; D013237:Stereoisomerism
D005609:Free Radicals
Free radicals; asymmetric synthesis; atropisomers; chirality; conformation; racemization; stereochemistry