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The Asymmetric Dialkylzinc Addition to Imines Catalyzed by [2.2]Paracyclophane-Based N,O-Ligands

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Stefan Dahmen^† and Stefan Bräse,

Kekul-Institut fr Organische Chemie und Biochemie der Rheinischen Friedrich-Wilhelms-Universitt Bonn, Gerhard-Domagk-Strasse 1, D-53121 Bonn, Germany, and Institut fr Organische Chemie der Rheinisch-Westflischen Technischen Hochschule Aachen, Professor-Pirlet-Strasse 1, D-52074 Aachen, Germany

J. Am. Chem. Soc., 2002, 124 (21), pp 5940–5941

DOI: 10.1021/ja025831e

Publication Date (Web): May 1, 2002

Copyright © 2002 American Chemical Society

Abstract

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The first highly enantioselective dialkylzinc addition to imines in the presence of catalytic amounts of N,O-ligands is reported. N-formyl-α-(p-tolysulfonyl)benzylamines are the readily available starting materials easily obtained in a one-pot synthesis from benzaldehydes, formamide, and p-tolylsulfinic acid. Upon deprotonation, the sulfinate is eliminated to give the acyl imine. The acyl imines further react with alkylzinc reagents in the presence of catalytic amounts of [2.2]paracyclophane-based N,O-ligands L* yielding the alkylated N-(1-phenylpropyl)formamides with excellent yields and enantioselectivities.

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History

Published In Issue May 29, 2002
Received February 6, 2002

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