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( S )‐Selective Kinetic Resolution and Chemoenzymatic Dynamic Kinetic Resolution of Secondary Alcohols
Author(s) -
Borén Linnéa,
MartínMatute Belén,
Xu Yongmei,
Córdova Armando,
Bäckvall JanE.
Publication year - 2005
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.200500758
Subject(s) - kinetic resolution , kinetic energy , resolution (logic) , chemistry , organic chemistry , physics , catalysis , computer science , enantioselective synthesis , classical mechanics , artificial intelligence
( S )‐Selective kinetic resolution was achieved through the use of a commercially available protease, which was activated with a combination of two different surfactants. The kinetic resolution (KR) process was optimized with respect to activation of the protease and to the acyl donor. The KR proved to be compatible with a range of functionalized sec ‐alcohols, giving good to high enantiomeric ratio values (up to >200). The enzymatic resolution was combined with a ruthenium‐catalyzed racemization to give an ( S )‐selective dynamic kinetic resolution (DKR) of sec ‐alcohols. The DKR process works under very mild reaction conditions to give the corresponding esters in high yields and with excellent enantioselectivities.