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Synlett 1997; 1997(SI): 523-524
DOI: 10.1055/s-1997-6125
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Enantioselective Alkylation of Aldehydes with Diethylzinc Catalyzed by C2-Symmetric Ligands

David R. Williams* , Mark G. Fromhold
  • *Department of Chemistry, Indiana University, Bloomington, Indiana 47405, U.S.A., FAX: (812) 855-8300, Internet: williamd@indiana.edu
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Publikationsdatum:
31. Dezember 2000 (online)

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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.

diethylzinc - enantioselective - C2-symmetric - ephedrine - catalyst