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Dynamic Asymmetric Hemithioacetal Transformation by Lipase‐Catalyzed γ‐Lactonization: In Situ Tandem Formation of 1,3‐Oxathiolan‐5‐one Derivatives
Author(s) -
Sakulsombat Morakot,
Zhang Yan,
Ramström Olof
Publication year - 2012
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.201102139
Subject(s) - tandem , lipase , transformation (genetics) , catalysis , chemistry , combinatorial chemistry , computer science , stereochemistry , organic chemistry , enzyme , materials science , biochemistry , composite material , gene
Dynamic hemithioacetal systems were efficiently generated in organic solvents and subsequently allowed to react with a range of lipases. This resulted in direct, dynamic asymmetric transformation of the systems, leading to optically active 1,3‐oxathiolan‐5‐one products. The tandem process identified lipase‐catalyzed lactonization as a useful method for the resolution of optimal constituents with high chemo‐ and stereoselectivities.