New Atropisomeric Amino Alcohol Ligands for Enantioselective Addition of Diethylzinc to Aldehydes

Efficient synthesis of several new atropisomeric amino alcohols having 1‐phenyl‐1H‐pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single‐crystal X‐ray measurement. The consequences of the size of the N‐substituents on enantioinduction were examined by employin...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2015-03, Vol.27 (3), p.216-222
Main Authors: Faigl, F., Deák, SZ, Erdélyi, ZS, Holczbauer, T., Czugler, M., Nyerges, M., Mátravölgyi, B.
Format: Article
Language:English
Subjects:
Alcohols
Aldehydes - chemistry
amino alcohol
Amino Alcohols - chemical synthesis
aromatic aldehyde
asymmetric catalysis
axial chirality
Catalysis
Chirality
Ligands
Organometallic Compounds - chemistry
selective hydrolysis
Single crystals
Special effects
Stereoisomerism
Synthesis
X-rays
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Summary:Efficient synthesis of several new atropisomeric amino alcohols having 1‐phenyl‐1H‐pyrrole skeleton are reported. Steric arrangements of the products were confirmed by a single‐crystal X‐ray measurement. The consequences of the size of the N‐substituents on enantioinduction were examined by employing the enantioselective catalytic addition of diethylzinc to a series of substituted benzaldehydes (yields 91–97%, up to 85% enantiomeric excess). The special effect of the ortho methoxy group of the substrate on the enantioinduction is also interpreted. Chirality 27:216–222, 2015. © 2014 Wiley Periodicals, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22415