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Optically Active Bicyclic N‐Heterocycles by Organocatalytic Asymmetric Michael Addition/Cyclization Sequences
Author(s) -
Worgull Dennis,
Dickmeiss Gustav,
Jensen Kim L.,
Franke Patrick T.,
Holub Nicole,
Jørgensen Karl Anker
Publication year - 2011
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.201100233
Subject(s) - aziridine , michael reaction , nucleophile , bicyclic molecule , optically active , organocatalysis , stereoselectivity , chemistry , cycloaddition , enantioselective synthesis , combinatorial chemistry , organic chemistry , catalysis , ring (chemistry)
Highly stereoselective one‐pot syntheses of various optically active N‐heterocyclic bicycles have been developed. The protocols are based on an organocatalytic, asymmetric Michael addition followed by a condensation/cycloaddition sequence to furnish aziridine carbonyls, β‐lactams, or octahydrobenzo[ c ]isoxazoles depending on the reaction conditions and applied nucleophiles.