[7] Either stereoisomer of can be converted to Ugi’s amine first by conversion to the acetate, then displacement with dimethylamine with complete stereoretention (see below for stereochemical outcome).

Additionally, Knochel, et al. reported a stereoselective synthesis of Ugi’s amine using the same acetylation/displacement strategy, but accesses (1R)-1-ferrocenylethanol from a Corey-Bakshi-Shibata reduction of acetylferrocene.

[8] Ugi’s amine is capable of promoting directed ortho lithiation diastereoselectively (with respect to planar chirality).

The high diastereoselectivity is independent of the electrophile used to trap the metalate, providing evidence for the stereoinductive step being lithiation and allowing broad synthetic utility of Ugi’s amine.

If the (S,Sp) or (R,Rp) diastereomers are desired, the first metalate can be trapped with TMSCl to block the more favored lithiation position.

Trapping with the desired electrophile and TBAF deprotection of the TMS group will provide the (S,Sp) or (R,Rp) diastereomer.

This is usually accomplished by quaternization of the amine with methyl iodide or acetic acid, which upon heating eliminates, resulting in a stable α-ferrocenylethyl cation intermediate.