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Switching the Enantioselectivities in Michael Addition of Pyrazolin‐5‐Ones to Nitroolefins by Benzoylthiourea Organocatalysts
Author(s) -
Wang Zhenyu,
Ban Shurong,
Yang Mengchen,
Li Qingshan
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201700491
Subject(s) - michael reaction , enantioselective synthesis , enantiomer , hydrogen bond , chemistry , organic chemistry , catalysis , molecule
Abstract A series ofnovel cinchonaalkaloid derived benzoylthiourea organocatalysts weresynthesized and applied as hydrogen bonding organocatalysts in the enantioselective Michael addition of pyrazolin‐5‐ones to nitroolefins. These organocatalysts promoted the Michael additions smoothly and gave the desired R or S enantiomers of the products flexibly in high yields with excellent enantioselectivities (up to 92 % ee and 89 % ee respectively) by the proper choice of organocatalysts.