Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by N-(9-Phenylfluoren-9-yl) β-Amino Alcohols
- 4 March 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (7) , 2108-2113
- https://doi.org/10.1021/jo9917083
Abstract
A set of secondary N-phenylfluorenyl beta-amino alcohols have been prepared and evaluated as catalysts for the enantioselective addition of diethylzinc to benzaldehyde. The influence of the substituents on the stereogenic centers of the ligand has been studied, and enantioselectivities up to 97% have been obtained. Those ligands with bulky groups in the carbinol stereocenter and small groups alpha to the nitrogen atom displayed the best catalytic activity and enantioselectivity. The most enantioselective ligand (4e) was found to possess general applicability for the enantioselective addition of diethylzinc to a variety of aromatic and aliphatic aldehydes.Keywords
This publication has 39 references indexed in Scilit:
- Asymmetric Addition of Dimethylzinc to Benzaldehyde Catalyzed by (2S)-3-exo-(Dimethylamino)isobornenol. A Theoretical Study on the Origin of EnantioselectionOrganometallics, 1998
- Origin of Enantioselectivities in Chiral β-Amino Alcohol Catalyzed Asymmetric Additions of Organozinc Reagents to Benzaldehyde: PM3 Transition State ModelingThe Journal of Organic Chemistry, 1998
- Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by Chiral Hydroxy AminalChemistry Letters, 1991
- Electroorganic chemistry. 129. Electroreductive synthesis of chiral piperazines and enantioselective addition of diethylzinc to aldehydes in the presence of the chiral piperazinesThe Journal of Organic Chemistry, 1991
- Polyfunctional, structurally defined catalysts for the enantioselective addition of dialkylzinc reagents to aldehydesThe Journal of Organic Chemistry, 1990
- Enantioselective addition of diethylzinc to aldehydes catalysed by secondary amino alcoholsJournal of the Chemical Society, Chemical Communications, 1989
- Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes using chiral pyrrolidinylmethanols and their metal saltsJournal of the American Chemical Society, 1987
- Enantioselective addition of diethylzinc to aldehydes catalyzed by polymer-supported chiral amino alcohols. Evidence for a two zinc species mechanismThe Journal of Organic Chemistry, 1987
- A new chiral catalyst for the highly enantioselective addition of dialkylzinc reagents to aliphatic aldehydesJournal of the Chemical Society, Chemical Communications, 1987
- Enantioface-differentiating (asymmetric) addition of alkyllithium and dialkylmagnesium to aldehydes by using (2S,2'S)-2-hydroxymethyl-1-[(1-alkylpyrrolidin-2-yl)methyl]pyrrolidines as chiral ligandsJournal of the American Chemical Society, 1979