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Highly Diastereo‐ and Enantioselective Formal Conjugate Addition of Nitroalkanes to Nitroalkenes by Chiral Ammonium Bifluoride Catalysis
Author(s) -
Ooi Takashi,
Takada Saki,
Doda Kanae,
Maruoka Keiji
Publication year - 2006
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200602787
Subject(s) - enantioselective synthesis , stereocenter , conjugate , catalysis , chemistry , ammonium , silylation , formal synthesis , combinatorial chemistry , organic chemistry , mathematics , mathematical analysis
A matter of control : A chiral quaternary ammonium bifluoride catalyst in combination with silyl nitronates results in the highly diastereo‐ and enantioselective formal conjugate addition of nitroalkanes to nitroalkenes (see scheme). The resulting 1,3‐dinitro compounds bear two defined stereocenters, which can serve as versatile chiral building blocks in organic synthesis.