Dr. Williams et Mg. Fromhold, ENANTIOSELECTIVE ALKYLATION OF ALDEHYDES WITH DIETHYLZINC CATALYZED BY C-2-SYMMETRICAL LIGANDS, Synlett, (5), 1997, pp. 523
The C-2-symmetric pyridine 1, incorporating two units of (-)-ephedrine
, is an effective catalyst for the enantioselective reactions of dieth
ylzinc with a series of aromatic aldehydes. The propanol products poss
ess the S-configuration. This result is a significant reversal of ster
eochemistry based upon literature precedents and our direct comparison
s with reactions catalyzed by the corresponding C-2-symmetric xylene 2
.