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

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 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).

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