Enantioselective Alkylation of Aldehydes with Diethylzinc Catalyzed by C2-Symmetric Ligands

Abstract
The C2-symmetric pyridine 1, incorporating two units of (-)-ephedrine, is an effective catalyst for the enantioselective reactions of diethylzinc with a series of aromatic aldehydes. The propanol products possess the S-configuration. This result is a significant reversal of stereochemistry based upon literature precendents and our direct comparisons with reactions catalyzed by the corresponding C2-symmetric xylene 2.

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