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Kinetic Resolution of Racemic Cyclic Sulfoxides Using Hydrolytic Enzymes
Author(s) -
Kiełbasiński Piotr,
Zwanenburg Binne,
Damen Theodorus J. G.,
Wieczorek Michał W.,
Majzner Wiesław R.,
Bujacz Grzegorz D.
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199910)1999:10<2573::aid-ejoc2573>3.0.co;2-g
Subject(s) - chemistry , kinetic resolution , hydrolysis , enantiomer , enzyme , resolution (logic) , organic chemistry , racemic mixture , kinetic energy , stereochemistry , enantioselective synthesis , catalysis , physics , quantum mechanics , artificial intelligence , computer science
Selected racemic trans‐2 ‐alkoxycarbonyl‐3,6‐dihydro‐2 H ‐thiopyran S ‐oxides 2a–h have been subjected to enzyme‐assisted hydrolysis under conditions of kinetic resolution to give the corresponding acids and recovered esters with moderate to high enantiomeric purities (up to 95%). The enantioselectivity of the reaction was found to be strongly dependent on the structures of the substrates used.