Iridium‐Catalyzed Asymmetric Intramolecular Allylic Amidation: Enantioselective Synthesis of Chiral Tetrahydroisoquinolines and Saturated Nitrogen Heterocycles | Zendy

Teichert Johannes F. | Zendy; FañanásMastral Martín | Zendy; Feringa Ben L. | Zendy

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Iridium‐Catalyzed Asymmetric Intramolecular Allylic Amidation: Enantioselective Synthesis of Chiral Tetrahydroisoquinolines and Saturated Nitrogen Heterocycles

Author(s) -

Teichert Johannes F.,

FañanásMastral Martín,

Feringa Ben L.

Publication year - 2011

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.201006039

Subject(s) - enantioselective synthesis , chemistry , intramolecular force , iridium , catalysis , allylic rearrangement , tetrahydroisoquinoline , enantiomer , asymmetric hydrogenation , combinatorial chemistry , organic chemistry

For the first time iridium catalysis has been used for the synthesis of chiral tetrahydroisoquinolines with excellent yields and high enantioselectivities (see scheme; cod=1,5‐cyclooctadiene, DBU=1,8‐diazabicyclo[5.4.0]undec‐7‐ene). These products are important chiral building blocks for the synthesis of biologically active compounds, in particular alkaloids.

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