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Dual stereoselection in the addition of diethylzinc to benzaldehyde by using highly structurally close ligands
Author(s) -
SánchezCarnerero Esther M. Márquez,
Engel Tomás De Las Casas,
Maroto Beatriz Lora,
Cerero Santiago De La Moya
Publication year - 2012
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.21994
Subject(s) - diethylzinc , chemistry , benzaldehyde , chirality (physics) , catalysis , transition state , dual role , dual (grammatical number) , zinc , combinatorial chemistry , computational chemistry , stereochemistry , organic chemistry , enantioselective synthesis , art , literature , chiral symmetry breaking , physics , quantum mechanics , quark , nambu–jona lasinio model
The screening of the catalytic activity in the diethylzinc reaction of a series of easily accessible (1 S )‐ketopinic‐acid derived hydroxyamides, designed by key structure modifications of a parent highly active related bis(hydroxyamide), has allowed to find the first case of dual stereoselection in highly structurally close ligands of such interesting chemically sustainable typology. The found striking dual stereoselection is explained on the basis of empiric models for the acting zinc catalysts and involved controlling transition states, which are supported by additional specific experimental structure‐activity tests. Chirality, 2012. © 2012 Wiley Periodicals, Inc.