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New Atropisomeric Amino Alcohol Ligands for Enantioselective Addition of Diethylzinc to Aldehydes
Author(s) -
Faigl F.,
Deák SZ.,
Erdélyi ZS.,
Holczbauer T.,
Czugler M.,
Nyerges M.,
Mátravölgyi B.
Publication year - 2015
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22415
Subject(s) - diethylzinc , chemistry , enantioselective synthesis , steric effects , alcohol , enantiomer , pyrrole , chirality (physics) , enantiomeric excess , catalysis , substrate (aquarium) , organic chemistry , stereochemistry , chiral symmetry breaking , physics , oceanography , quantum mechanics , quark , geology , nambu–jona lasinio model
Efficient synthesis of several new atropisomeric amino alcohols having 1‐phenyl‐1 H ‐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.