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 | Zendy

Gnamm Christian | Zendy; Krauter Caroline M. | Zendy; Brödner Kerstin | Zendy; Helmchen Günter | Zendy

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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.

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