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N‐Heterocyclic Carbene Catalyzed [3+2] Cycloaddition of Enals with Masked Cinnamates for the Asymmetric One‐Pot Synthesis of Adipic Acid Derivatives
Author(s) -
Chen XiangYu,
Li Sun,
Sheng He,
Liu Qiang,
Jafari Ehsan,
von Essen Carolina,
Rissanen Kari,
Enders Dieter
Publication year - 2017
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.201703579
Subject(s) - chemistry , cyclopentanone , cinnamates , cycloaddition , catalysis , adipic acid , carbene , organic chemistry , combinatorial chemistry
Abstract A novel short entry to 3,4‐disubstituted adipic acids has been developed by employing an asymmetric NHC‐catalyzed [3+2] cycloaddition of enals with masked cinnammates in moderate to good yields and high stereoselectivities. The synthetic utility of the protocol was demonstrated by the basic conversion of the masked cyclopentanone intermediates to 3 S ,4 S ‐disubstituted adipic acid precursors of pharmaceutically important gababutins.