Enantioselective Addition of Organozinc Reagents to Carbonyl Compounds

ChemInform ◽  
2006 ◽  
Vol 37 (24) ◽  
Author(s):  
Miguel Yus ◽  
Diego J. Ramon
Keyword(s):  
Carbonyl Compounds ◽  
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).

Recent Advances in the Synthesis of Enantiomerically Enriched Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols through Addition of Organometallic Reagents to Carbonyl Compounds

Synthesis ◽  
2020 ◽  
Vol 52 (13) ◽  
pp. 1855-1873
Author(s):  
Senthil Narayanaperumal ◽  
Ricardo S. Schwab ◽  
Wystan K. O. Teixeira ◽  
Danilo Yano de Albuquerque
Keyword(s):  
Carbonyl Compounds ◽  
Building Blocks ◽  
Short Review ◽  
Biological Properties ◽  
Enantioselective Synthesis ◽  
Grignard Reagents ◽  
Organometallic Reagents ◽  
Important Family ◽  
Organolithium Reagents ◽  
Organozinc Reagents

Enantiomerically enriched diaryl, aryl heteroaryl, and dihetero­aryl alcohols are an important family of compounds known for their biological properties. Moreover, these molecules are highly privileged scaffolds used as building blocks for the synthesis of pharmaceutically relevant products. This short review provides background on the enantioselective arylation and heteroarylation of carbonyl compounds, as well as, the most significant improvements in this field with special emphasis on the application of organometallic reagents.1 Introduction2 Background on the Enantioselective Synthesis of Diaryl, Aryl Heteroaryl, and Diheteroaryl Alcohols3 Organozinc Reagents4 Organolithium Reagents5 Grignard Reagents6 Organoaluminum Reagents7 Organotitanium Reagents8 Organobismuth Reagents9 Miscellaneous10 Conclusion

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.

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