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Asymmetric [3+3] Cycloaddition of Donor−Acceptor Aziridines with N , N ‐Dialkyl‐3‐vinylanilines to Construct Highly Functionalized Enantioenriched Tetrahydroisoquinolines
Author(s) -
Kim Seungyeon,
Kim SungGon
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900073
Subject(s) - chemistry , enantioselective synthesis , cycloaddition , acceptor , catalysis , medicinal chemistry , tetrahydroisoquinoline , stereochemistry , combinatorial chemistry , organic chemistry , physics , condensed matter physics
A diastereo‐ and enantioselective [3+3] cycloaddition of donor−acceptor aziridines with N , N ‐dialkyl‐3‐vinylanilines has been established using a Mg(OTf) 2 /bisoxazoline catalyst, providing highly functionalized tetrahydroisoquinolines in good yields and with high levels of stereocontrol. A wide variety of N , N ‐dialkyl‐3‐vinylanilines, such as m ‐ N , N ‐dimethylaminophenyl α,β‐unsaturated phenyl ketones and 3‐( m‐N , N ‐dimethylaminophenyl)acrylates, as well as donor−acceptor N ‐tosylaziridines, have been applied in this asymmetric catalytic protocol.