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Synergistic Catalysis for the Asymmetric [3+2] Cycloaddition of Vinyl Aziridines with α,β‐Unsaturated Aldehydes
Author(s) -
Næsborg Line,
Tur Fernando,
Meazza Marta,
Blom Jakob,
Halskov Kim Søholm,
Jørgensen Karl Anker
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.201604995
Subject(s) - pyrrolidine , cycloaddition , catalysis , chemistry , molecule , combinatorial chemistry , organic chemistry , enantioselective synthesis
The first asymmetric [3+2] cycloaddition of vinyl aziridines with α,β‐unsaturated aldehydes, based on synergistic catalysis, is disclosed. This methodology allows the formation of attractive pyrrolidine structures in good yields (up to 84 %), moderate diastereoselectivity, and high enantioselectivity values (up to >99 % ee ). Additionally, a tricyclic pyrrolidine core structure found in biologically active molecules was synthesized in a one‐pot fashion by using the presented reaction concept. Finally, a mechanistic proposal is outlined.