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Heterogeneous Acid‐Catalyzed Racemization of Tertiary Alcohols
Author(s) -
Görbe Tamás,
Lihammar Richard,
Bäckvall JanE.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704691
Subject(s) - racemization , enantiomer , enantioselective synthesis , tertiary alcohols , chemistry , protein tertiary structure , kinetic resolution , organic chemistry , catalysis , resolution (logic) , combinatorial chemistry , computer science , biochemistry , artificial intelligence
Tertiary alcohols are important structural motifs in natural products and building blocks in organic synthesis but only few methods are known for their enantioselective preparation. Chiral resolution is one of these approaches that leaves one enantiomer (50 % of the material) unaffected. An attractive method to increase the efficiency of those resolutions is to racemize the unaffected enantiomer. In the present work, we have developed a practical racemization protocol for tertiary alcohols. Five different acidic resin materials were tested. The Dowex 50WX8 was the resin of choice since it was capable of racemizing tertiary alcohols without any byproduct formation. Suitable solvents and a biphasic system were investigated, and the optimized system was capable of racemizing differently substituted tertiary alcohols.