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Stereoelectronic Effects and Chiral Recognition: A Natural System of Relationships between Chiral Compounds based on Selectivities in the Formation of Acetals
Author(s) -
Noe Christian R.,
Knollmüller Max,
Göstl Georg,
Oberhauser Berndt,
Völlenkle Horst
Publication year - 1987
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198704421
Subject(s) - enantiomer , chemistry , group (periodic table) , stereochemistry , hydrogen bond , chirality (physics) , preference , hydrogen atom , organic chemistry , molecule , chiral symmetry , mathematics , physics , quantum mechanics , nambu–jona lasinio model , quark , statistics
“Like and like go well together,” underscores the finding that the symmetrical dilactols are preferentially formed upon reaction of a 1:1 mixture of 1 and 2 with acids. In one view at the exocyclic CO bond in 1 , C2 is surrounded in a clockwise sense by a bulky group, a linear group, and a hydrogen atom (A configuration). In contrast 2 has B‐configuration. The preference for A‐A and BB products could help to explain many enantiomeric selectivities better.