ISSN:
0009-2940
Keywords:
Diastereoselectivity
;
Effect, kinetic
;
Effect, stereoelectronic
;
Etherification
;
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Stereoelectronic Effects and Chiral Recognition, I. - Diastereoselective Formation of Ethers from AlkylarylcarbinolsAcid-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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19941270213
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