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Asymmetric Diels–Alder Cycloadditions of Trifluoromethylated Dienophiles Under Trienamine Catalysis
Author(s) -
Yuan Xin,
Zhang ShanJun,
Du Wei,
Chen YingChun
Publication year - 2016
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.201600989
Subject(s) - chemistry , benzylamine , trifluoromethyl , stereoselectivity , reductive amination , amination , catalysis , amine gas treating , organic chemistry , trifluoromethylation , organocatalysis , enantioselective synthesis , medicinal chemistry , alkyl
β‐Trifluoromethyl (CF 3 ) enones were proved to act as good dienophiles in asymmetric normal‐electron‐demand Diels–Alder cycloadditions with 2,4‐dienals under trienamine catalysis with a chiral secondary amine. The sequential reductive amination transformations with benzylamine produced cis‐ and trans‐ fused chiral trifluoromethylated octahydroisoquinolines in a diastereodivergent manner by using NaBH(OAc) 3 and NaBH 3 CN as the reductants, respectively. Moreover, other types of activated alkenes that bear a CF 3 group have also been successfully utilized to construct a diverse range of chiral cyclic frameworks in high stereoselectivity.