Publication detail

Camphor-annelated imidazolines with various N1 and C2 pendants as tunable ligands for nitroaldol reactions

Authors: Tydlitát Jiří | Bureš Filip | Kulhánek Jiří | Mloston Grzegorz | Růžička Aleš

Year: 2012

Type of publication: článek v odborném periodiku

Name of source: Tetrahedron Asymmetry

Publisher name: Elsevier Science BV

Place: Amsterdam

Page from-to: 1010-1018

Titles:

Language	Name	Abstract	Keywords
cze	Imidazoliny na bázi kafru s různými substituenty v polohách N1 a C2 jako ligandy v nitroaldolové kondenzaci	Z (1R,2S,3R)-kafrdiaminu and (hetero)aromatických imidátu byly připraveny NH-imidazoliny s anelovaným kruhem kafru. Následná N-modifikace methylací, acylací, benzoylací a sulfonací poskytla další ligandy ve formě dvou regioizomerů. Tyto sloučeniny byly testovány v Henryho reakci a byly studovány elektronové vlivy substituentů na N1 a C2 poizcích imidazolinu.	imidazolin; ligand; měďnatý iont; Henryho reakce
eng	Camphor-annelated imidazolines with various N1 and C2 pendants as tunable ligands for nitroaldol reactions	Starting from (1R,2S,3R)-camphordiamine and (hetero)aromatic imidates and orthoformate, nine new camphor-annelated NH-imidazolines were synthesized. Subsequent N-modification was carried out via methylation, acylation, benzoylation, and sulfonylation. Two regioisomers were usually isolated with the ratios reflecting the structure of the starting NH-imidazoline and the electrophile used. All of the successfully prepared N1- and C2-substituted camphor-annelated imidazolines were applied to the asymmetric version of a Cu(II)-catalyzed Henry reaction. The electronic effects of both N1- and C2-pendants on the chemical and asymmetric outcomes of the nitroaldol reaction have been studied and discussed.	imidazoline; ligand; copper ion; Henry reaction; ligand tuning

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