The Asymmetric Dialkylzinc Addition to Imines Catalyzed by [2.2]Paracyclophane-Based N,O-Ligands
- 1 May 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 124 (21) , 5940-5941
- https://doi.org/10.1021/ja025831e
Abstract
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.Keywords
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