Self and nonself recognition of chiral catalysts: The origin of nonlinear effects in the amino-alcohol catalyzed asymmetric addition of diorganozincs to aldehydes

10.1002/tcr.1 ◽  
2001 ◽  
Vol 1 (2) ◽  
pp. 85-100 ◽  
Author(s):  
Ryoji Noyori ◽  
Seiji Suga ◽  
Hiromasa Oka ◽  
Masato Kitamura
Keyword(s):  
Amino Alcohol ◽  
Nonlinear Effects ◽  
Chiral Catalysts ◽  
Asymmetric Addition ◽  
Nonself Recognition

A new pyrrolidine-derived atropisomeric amino alcohol as a highly efficient chiral ligand for the asymmetric addition of diethylzinc to aldehydes

2014 ◽  
Vol 55 (50) ◽  
pp. 6891-6894 ◽  
Author(s):  
Ferenc Faigl ◽  
Zsuzsa Erdélyi ◽  
Szilvia Deák ◽  
Miklós Nyerges ◽  
Béla Mátravölgyi
Keyword(s):  
Amino Alcohol ◽  
Chiral Ligand ◽  
Asymmetric Addition ◽  
Highly Efficient

Polystyrene-Supported Amino Alcohol Ligands for the Heterogeneous Asymmetric Addition of Phenyl Zinc Reagents to Aldehydes.

ChemInform ◽  
2006 ◽  
Vol 37 (15) ◽  
Author(s):  
David Castellnou ◽  
Montserrat Fontes ◽  
Ciril Jimeno ◽  
Daniel Font ◽  
Lluis Sola ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Asymmetric Addition

ChemInform Abstract: A New Pyrrolidine-Derived Atropisomeric Amino Alcohol as a Highly Efficient Chiral Ligand for the Asymmetric Addition of Diethylzinc to Aldehydes.

ChemInform ◽  
2015 ◽  
Vol 46 (18) ◽  
pp. no-no
Author(s):  
Ferenc Faigl ◽  
Zsuzsa Erdelyi ◽  
Szilvia Deak ◽  
Miklos Nyerges ◽  
Bela Matravoelgyi
Keyword(s):  
Amino Alcohol ◽  
Chiral Ligand ◽  
Asymmetric Addition ◽  
Highly Efficient

Novel Polymer-Bound Amino Alcohol Ligands for the Asymmetric Addition of Diethylzinc to Aldehydes.

ChemInform ◽  
2007 ◽  
Vol 38 (45) ◽  
Author(s):  
Philip C. Bulman Page ◽  
Steven M. Allin ◽  
Suzanne J. Dilly ◽  
Benjamin R. Buckley
Keyword(s):  
Amino Alcohol ◽  
Asymmetric Addition

scholarly journals Enantioselective Conjugate Addition of Catalytically Generated Zinc Homoenolate

2021 ◽  
Author(s):  
Yoshiya Sekiguchi ◽  
Naohiko Yoshikai
Keyword(s):  
Amino Alcohol ◽  
Ring Opening ◽  
Addition Reaction ◽  
Aldol Condensation ◽  
Nonlinear Effects ◽  
Conjugate Addition ◽  
Unsaturated Ketone ◽  
Lower Reactivity

<div> <div> <div> <p>We report herein an enantioselective conjugate addition reaction of a zinc homoenolate, catalytically generated via ring opening of a cyclopropanol, to an α,β-unsaturated ketone. The reaction is promoted by a zinc aminoalkoxide catalyst generated from Et2Zn and a chiral β-amino alcohol to afford 1,6- diketones, which undergo, upon heating, intramolecular aldol condensation to furnish highly substituted cyclopentene derivatives with good to high enantioselectivities. The reaction has proved applicable to various 1-substituted cyclopropanols as well as chalcones and related enones. The chiral amino alcohol has proved to enable ligand-accelerated catalysis of the homoenolate generation and its conjugate addition. Positive nonlinear effects and lower reactivity of a racemic catalyst have been observed, which can be attributed to a stable and inactive heterochiral zinc aminoalkoxide dimer. </p> </div> </div> </div>

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