Fig. 4: Synthetic steps transferring chiral information.
From: Enantioselective synthesis of a two-fold inherently chiral molecular nanographene
a, A Mitsunobu-like SN2 reaction is a plausible mechanism for the observed stereochemical results in the Hendrickson reaction for (S,S)-6. As shown by X-ray crystallographic analysis of (S,S,Sa,M,M)-1, there is an inversion of configuration for the two stereogenic centres of the indane moiety (green). b, A plausible mechanism for the observed enantiospecificity in the Scholl reaction for (S,S,Sa)-7 is based on the effect of the indane closest to the reaction centre hindering the nucleophilic attack of the adjacent phenyl group (purple) from the Re face.
