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Asymmetric Synthesis of Substituted Thiolanes through Domino Thia‐Michael–Henry Dynamic Covalent Systemic Resolution using Lipase Catalysis
Author(s) -
Zhang Yan,
Vongvilai Pornrapee,
Sakulsombat Morakot,
Fischer Andreas,
Ramström Olof
Publication year - 2014
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201301033
Subject(s) - domino , chemistry , stereocenter , lipase , michael reaction , enantiomer , cascade reaction , catalysis , enantioselective synthesis , nitroaldol reaction , combinatorial chemistry , stereochemistry , organic chemistry , enzyme
Abstract Dynamic systems based on consecutive thia‐Michael and Henry reactions were generated and transformed using lipase‐catalyzed asymmetric transformation. Substituted thiolane structures with three contiguous stereocenters were resolved in the process in high yields and high enantiomeric excesses.