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| - Enantioselective Addition of Vinylzinc Reagents to AldehydesCatalyzed by Modular Ligands Derived from Amino Acids
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| - A series of N-acylethylenediamine-based ligands were synthesized from Boc-protected amino acids.The ligands were screened for the ability to catalyze the asymmetric addition of vinylzinc reagentsto aldehydes. Three sites of diversity on the ligands were optimized for this reaction using apositional scanning approach. The optimized ligand 3d was found to catalyze the formation of 15different (E)-allylic alcohols with enantioselectivities that ranged from 52 to 91% ee and yieldsthat ranged from 40 to 90%. This ligand was especially effective for the reaction of aromaticaldehydes with vinylzinc reagents derived from bulky terminal alkynes. Ligand 3d catalyzed theaddition of (E)-(3,3-dimethylbut-1-enyl)(ethyl)zinc to 2-naphthaldehyde to give (R,E)-4,4-dimethyl-1-(naphthalene-1-yl)pent-2-en-1-ol in 89% ee. The ee of this product could be increased to 97%through a single recrystallization.
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