Asymmetric Synthesis of 2 H ‐Azirines with a Tetrasubstituted Stereocenter by Enantioselective Ring Contraction of Isoxazoles | Zendy

Okamoto Kazuhiro | Zendy; Nanya Atsushi | Zendy; Eguchi Akira | Zendy; Ohe Kouichi | Zendy

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Asymmetric Synthesis of 2 H ‐Azirines with a Tetrasubstituted Stereocenter by Enantioselective Ring Contraction of Isoxazoles

Author(s) -

Okamoto Kazuhiro,

Nanya Atsushi,

Eguchi Akira,

Ohe Kouichi

Publication year - 2018

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.201710920

Subject(s) - stereocenter , enantioselective synthesis , substituent , chemistry , rhodium , stereochemistry , isomerization , diene , catalysis , ligand (biochemistry) , ring (chemistry) , combinatorial chemistry , organic chemistry , receptor , biochemistry , natural rubber

Highly strained 2 H ‐azirines with a tetrasubstituted stereocenter were synthesized by the enantioselective isomerization of isoxazoles with a chiral diene–rhodium catalyst system. The effect of ligands and the coordination behavior support the proposed catalytic cycle in which the coordination site is fixed in favor of efficient enantiodiscrimination by a bulky substituent of the ligand. In silico studies also support the existence of a rhodium–imido complex as a key intermediate for enantiodiscrimination.

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