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Title: Stereo- and regiochemistry in the (asymmetric) cycloaddition reaction of 5-chloro-2(1H)-pyrazinones with cyclic and monosubstituted alkenes and with a N-acryloyl substituted chiral auxiliary
Authors: Rombouts, FJR ×
Vanraes, DAJ
Wynendaele, J
Loosen, PK
Luyten, Ingrid
Toppet, Suzanne
Compernolle, Frans
Hoornaert, GJ #
Issue Date: Jan-2001
Publisher: Pergamon-elsevier science ltd
Series Title: Tetrahedron vol:57 issue:15 pages:3209-3220
Abstract: The cycloaddition of 5-chloro-2(1H)-pyrazinones 1 with various dienophiles was used to generate the corresponding 2,5-diazabicyclo[2.2.2]octanes. Following reduction or hydrolysis of the bridged adducts, the regio- and stereochemical structure was determined by analysis of the coupling and NOE patterns in the H-1 NMR spectra. With symmetric dienophiles the endo adducts are formed exclusively. The regiochemistry for the reaction of 1 with methyl acrylate and ethyl vinyl ether, and the asymmetric induction found with the N-acryloyl substituted chiral auxiliary (4S)-4-isopropyl-1-methyltetrahydro-2H-imidazol-2-one, largely depend on the electron donating or attracting properties and size of the 3-substituents of i. (C) 2001 Elsevier Science Ltd. All rights reserved.
URI: 
ISSN: 0040-4020
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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