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Breaking Symmetry with Symmetry: Bifacial Selectivity in the Asymmetric Cycloaddition of Anthracene Derivatives
Author(s) -
RodríguezEscrich Carles,
Davis Rebecca L.,
Jiang Hao,
Stiller Julian,
Johansen Tore K.,
Jørgensen Karl Anker
Publication year - 2013
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.201300142
Subject(s) - anthracene , cycloaddition , enantioselective synthesis , computer science , selectivity , yield (engineering) , chemistry , combinatorial chemistry , catalysis , computational chemistry , photochemistry , organic chemistry , physics , thermodynamics
Push to activate : A new catalytic strategy for the activation of anthracene derivatives has been developed. From symmetrical starting materials, enantioselective cycloaddition reactions can be achieved by employing a C 2 ‐symmetric aminocatalyst. This selectivity is due to the gain or loss of conjugation between the enamine and the anthracene in the two transition‐state structures. This methodology is demonstrated in 14 examples with 70–96 % yield and 76–95 % ee.