Design of novel chiral N,N,O-tridentate phenanthroline ligands and their application to enantioselective addition of organozinc reagents to aldehydes

2014 ◽  
Vol 50 (87) ◽  
pp. 13224-13227 ◽  
Author(s):  
Yuki Naganawa ◽  
Tomoya Namba ◽  
Tomotaka Aoyama ◽  
Kentaro Shoji ◽  
Hisao Nishiyama
Keyword(s):  
The Novel ◽  
Tridentate Ligands ◽  
Enantioselective Addition ◽  
Organozinc Reagents ◽  
Phenanthroline Ligands

The novel chiral N,N,O-tridentate ligands (BinThro) containing binaphthyl and phenanthroline units were developed. The enantioselective organozinc addition to aldehydes was performed in the presence of BinThro (S)-1 with up to 95% ee.

Enantioselective Addition of Organozinc Reagents to Aldehydes Catalyzed by 3,3′-Bis(diphenylphosphinoyl)-BINOL

2005 ◽  
Vol 347 (11-13) ◽  
pp. 1561-1568 ◽  
Author(s):  
Manabu Hatano ◽  
Takashi Miyamoto ◽  
Kazuaki Ishihara
Keyword(s):  
Enantioselective Addition ◽  
Organozinc Reagents

Enantioselective addition of organozinc reagents to carbonyl compounds

2005 ◽  
Vol 77 (12) ◽  
pp. 2111-2119 ◽  
Author(s):  
Miguel Yus ◽  
Diego J. Ramón
Keyword(s):  
Carbonyl Compounds ◽  
Titanium Tetraisopropoxide ◽  
Enantioselective Addition ◽  
Organozinc Reagents

Different chiral camphorsulfonamide derivatives containing a hydroxy or a sulfonamido functionality, as well as chiral 1,2-hydroxysulfonamides, have been evaluated as chiral promoters in the classical enantioselective addition of dialkylzinc reagents to aldehydes in the presence of titanium tetraisopropoxide (ee up to 96 %). Surprisingly, ligands with a structure of isoborneol are able to promote the related unknown addition to ketones (ee >99 %), the best ligand being the exo-diol derived from 1,2-trans-biscamphorsulfonamidocyclohexane (HOCSAC).

Synthesis of Chiral Tridentate Ligands Embodying the Bispidine Framework and their Application in the Enantioselective Addition of Diethylzinc to Aldehydes

2011 ◽  
Vol 396-398 ◽  
pp. 1236-1243 ◽  
Author(s):  
Yue Cheng Zhang ◽  
Jing Yuan Gao ◽  
Nai Yue Shi ◽  
Ji Quan Zhao
Keyword(s):  
Catalytic Reaction ◽  
Aromatic Aldehydes ◽  
Aliphatic Aldehyde ◽  
Chiral Center ◽  
Hydroxyl Group ◽  
High Yield ◽  
Chiral Ligand ◽  
Tridentate Ligands ◽  
Reaction Systems ◽  
Enantioselective Addition

Several new chiral tridentate ligands with the bispidine moiety were synthesized from N-alkyl bispidines and chiral amino (or hydroxyl) acids. The synthesized ligands were used as catalysts in the enantioselective addition of diethylzinc to several aromatic aldehydes and an aliphatic aldehyde. High yield and enantioselectivity were received in the cases of aromatic aldehydes as substrates especially when the employed chiral ligand has a hydroxyl group attached to the chiral center. The effect of the structure, the amount of tridentate chiral ligands, solvent and temperature on the enantioselectivity of the addition products were studied. A possible mechanism for the addition of diethylzinc to aldehydes in the presence of bispidine-derived ligands were proposed based upon the catalytic reaction results and referred to the mechanisms proposed for other reaction systems in literatures.

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