Modification of (1R,2S)-1,2-Diphenyl-2-aminoethanol for the Highly Enantioselective, Asymmetric Alkylation ofN-Diphenylphosphinoyl Arylimines with Dialkylzinc
| Autor: | Fan Jiang, Xiao-Mei Zhang, Hai-Le Zhang, Xin Cui, Yaozhong Jiang, Aiqiao Mi, Liu-Zhu Gong, Yun-Dong Wu |
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| Rok vydání: | 2004 |
| Předmět: |
Models
Molecular Alkylation Molecular Structure Chemistry Organic Chemistry Chiral ligand Enantioselective synthesis chemistry.chemical_element Stereoisomerism General Chemistry Zinc Diethylzinc Ligands Catalysis chemistry.chemical_compound Ethanolamines Organometallic Compounds Organic chemistry Imines 2-Aminoethanol Enantiomer |
| Zdroj: | Chemistry - A European Journal. 10:1481-1492 |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.200305418 |
| Popis: | Experimental studies on the modification of (1R,2S)-1,2-diphenyl-2-aminoethanol, which is used to promote the alkylation of N-diphenylphosphinoyl benzalimine with diethylzinc, revealed that N-monosubstituted amino alcohols exhibited higher enantioselectivities than their N,N-disubstituted counterparts and imino alcohols. Application of the optimal chiral ligand 3 c to activate the reaction of N-diphenylphosphinoyl arylimines with diethylzinc and dibutylzinc resulted in excellent enantiomeric selectivities of up to 98 % ee. The origin of the experimentally observed enantioselectivities was revealed by density functional calculations (B3LYP/6-31G*) on the transition structures of several model reactions. |
| Databáze: | OpenAIRE |
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