Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines Promoted by 2-Azanorbornylmethanols
- 28 March 1998
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 63 (8) , 2530-2535
- https://doi.org/10.1021/jo9718096
Abstract
A set of new β-amino alcohols 2, with the 2-azanorbornyl framework, has been prepared and evaluated as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines 1. By variation of the substitution pattern in the ligand, ee's up to 92% could be obtained. Although a stoichiometric amount of the ligand was used, about 90% of it could be recovered during the workup. Amino alcohol 2b, that gave the best enantioselectivities in the stoichiometric reaction, was also applied in a catalytic process, and ee's up to 85% were achieved using 0.25 equiv of the ligand, which is the highest ee obtained so far using that catalytic amount of the ligand. Addition products 3 could be converted into the free amines 4 without racemization by acidic hydrolysis. The utility of ligands 2 as catalysts in the addition of diethylzinc to benzaldehyde has also been investigated, and ee's up to 75% were achieved.Keywords
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