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Stereoelektronische Effekte und chirale Erkennung, I. Diastereoselektive Etherbildungen aus Alkylarylcarbinolen
Author(s) -
Noe Christian R.,
Knollmüller Max,
Dungler Karin,
Miculka Christian
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19941270213
Subject(s) - diastereomer , chemistry , stereochemistry , kinetic control , organic chemistry , catalysis
Stereoelectronic Effects and Chiral Recognition, I. — Diastereoselective Formation of Ethers from Alkylarylcarbinols Acid‐catalysed etherification of various alkylarylcarbinols 1 leads to a mixture of diastereomeric products 2 and 3 . As found in the closely related formation of diastereomeric acetals, the ratio 2/3 is shown to be time‐dependent. Preferred formation of the meso ‐diastereomer 3 under kinetic condition and preferred formation of the racemic diastereomer 2 under thermodynamic conditions is observed. A reaction path based on π‐π interactions and stereoelectronic effects is presented to explain experimental results.