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Dihydropyridones: Catalytic Asymmetric Synthesis, N‐ to C‐Sulfonyl Transfer, and Derivatizations
Author(s) -
Simal Carmen,
Lebl Tomas,
Slawin Alexandra M. Z.,
Smith Andrew D.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201109061
Subject(s) - sulfonyl , chemistry , photoisomerization , catalysis , tosyl , ammonium , medicinal chemistry , organic chemistry , combinatorial chemistry , isomerization , alkyl
Benzotetramisole (1) promotes the reaction of ammonium enolates derived from arylacetic acids with N ‐tosyl‐α,β‐unsaturated ketimines, thus giving dihydropyridones with high diastereo‐ and enantiocontrol (see scheme). These products readily undergo N‐ to C‐sulfonyl photoisomerization and are derivatized to afford stereodefined piperidines and tetrahydropyrans.