A series of new chiral squaric amino alcohols derived from (R)-(+)-camphor and squaric acid were synthesized, and applied to the enantioselective reduction of prochiral ketones with borane to give secondary alcohols with excellent enantiomeric excesses (up to 99%).

It is found that the addition of hexamethylphosphoramide to the solution of an alkyne, Et2Zn, and (S)-1,1 -bi-2-naphthol in methylene chloride allows the generation of an alkynylzinc at room temperature and shows highly enantioselective additions to aldehydes. The mild condition for the formation of the alkynylzinc reagent enables the use of functional alkynes in this asymmetric reaction with excellent enantioselectivity. It avoids the reflux of the toluene solutions of the alkynes and Et2Zn as previously reported.

In the presence of a catalytic amount of a simple copper salt, the coupling of imidazole with arylboronic acids was performed in methanol to give corresponding N-arylimidazoles in almost quantitative yields; this coupling reaction could also be performed in aqueous solutions to give N-arylimidazoles in excellent yields.

Novel homochiral molecular tweezers comprised of two chiral macrocyclic polyamine skeletons have been developed. These homochiral artificial receptors exhibit excellent chiral recognition ability toward the enantiomers of L-and D-amino acid derivatives (up to KL/KD=7.9, G0=−5.12 kJ mol−1) in CHCl3 at 25.0℃.

Chiral metallomicellar supramolecular systems composed of lipophilic l-histidinol have been investigated for their catalytic activities and enantioselectivities in the hydrolysis of N-protected -amino acid esters. Kinetic evidence suggests that the mechanism of the deacylation promoted by ligand 4a with a hydroxyl group and 2a lacking a hydroxyl group is different. The apparent pKa of Zn2+-4a is 6.8 in the micelllar aggregate. The highest enantioselectivity in hydrolysis of R(S)-C12-Leu-PNP (kS/kR=3.01) was obtained with 4a-Zn2+ as catalyst.