Memory of chirality
‘Memory of chirality’ reaction is defined as a formal substitution at an sp3 stereogenic centre that proceeds stereospecifically, even though the reaction proceeds by trigonalization of that centre, and despite the fact that no other permanently chiral elements are present.1 Our idea stem from the outstanding observation by E. I. Heiba and R. M. Dessau2 when they obtained optically active lactone upon radical cyclization of optically active propargyl ester whose asymmetric centre involves the hydrogen to be abstracted. We are elongating this strategy towards amide substrates with varying N-substitutions.
1. Zhao, H.; Hsu, D. C.; Carlier, P. R. Synthesis 2005, 1-16.
2. Heiba, E. I.; Dessau, R. M. J. Am. Chem. Soc. 1967, 89, 2238.