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Letter

Dimethylzinc-Mediated Addition of Alkenylzirconocenes to α-Keto and α-Imino Esters

Supporting Info

Peter Wipf* and Corey R. J. Stephenson

Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260

Org. Lett., 2003, 5 (14), pp 2449–2452

DOI: 10.1021/ol0347141

Publication Date (Web): June 10, 2003

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, pwipf+@pitt.edu

Abstract

Hydrozirconation of alkynes followed by in situ transmetalation to dimethylzinc and 1,2-addition to activated ketones and N-diphenylphosphinoylimines leads to tertiary allylic alcohols and amines in high overall yield. With 8-phenylmenthol as the chiral auxiliary, si-face attack proceeds in good to excellent diastereoselectivities.

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Published In Issue July 10, 2003
Received April 29, 2003

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Letter

Dimethylzinc-Mediated Addition of Alkenylzirconocenes to α-Keto and α-Imino Esters

Abstract

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SciFinder Links

History

Recommend & Share

Related Content

Diastereoselective and Enantioselective Rh(I)-Catalyzed Additions of Arylboronic Acids to N-tert-Butanesulfinyl and N-Diphenylphosphinoyl Aldimines

Palladium-Catalyzed Highly Diastereoselective Oxidative Cascade Cyclization Reactions

Enantioselective Reduction of Imines Catalyzed by a Rhenium(V)−Oxo Complex

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