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Stereoselective Synthesis of 2,6‐Disubstituted Piperidines Using the Iridium‐Catalyzed Allylic Cyclization as Configurational Switch: Asymmetric Total Synthesis of (+)‐241 D and Related Piperidine Alkaloids
Author(s) -
Gnamm Christian,
Krauter Caroline M.,
Brödner Kerstin,
Helmchen Günter
Publication year - 2009
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.200802525
Subject(s) - epimer , iridium , stereoselectivity , enantiomer , piperidine , chemistry , alkaloid , total synthesis , allylic rearrangement , enantioselective synthesis , selectivity , catalysis , stereochemistry , combinatorial chemistry , organic chemistry
Pressing the configurational switch : Use of enantiomeric Ir catalysts allows the vinylpiperidine building blocks 2 a and 2 b to be synthesized with high selectivity. Total syntheses of the dendrobate alkaloid (+)‐241 D, its C6‐epimer, and a spruce alkaloid are presented as applications.