Borane‐Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction‐Induced Electrocyclization | Zendy

Maier Alexander F. G. | Zendy; Tussing Sebastian | Zendy; Zhu Hui | Zendy; Wicker Garrit | Zendy; Tzvetkova Pavleta | Zendy; Flörke Ulrich | Zendy; Daniliuc Constantin G. | Zendy; Grimme Stefan | Zendy; Paradies Jan | Zendy

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Borane‐Catalyzed Synthesis of Quinolines Bearing Tetrasubstituted Stereocenters by Hydride Abstraction‐Induced Electrocyclization

Author(s) -

Maier Alexander F. G.,

Tussing Sebastian,

Zhu Hui,

Wicker Garrit,

Tzvetkova Pavleta,

Flörke Ulrich,

Daniliuc Constantin G.,

Grimme Stefan,

Paradies Jan

Publication year - 2018

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.201804777

Subject(s) - stereocenter , hydride , quinoline , borane , chemistry , catalysis , boranes , medicinal chemistry , combinatorial chemistry , organic chemistry , boron , enantioselective synthesis , hydrogen

The borane‐catalyzed synthesis of quinoline derivatives bearing tetrasubstituted stereocenters from vinyl anilines has been developed. Mechanistic studies and quantum‐mechanical investigations support the hydride abstraction/electrocyclization/hydride addition mechanism. The products were obtained in up to 99 % yield with a diastereoselectivity of >99 % in favour for the 3a‐5‐ cis isomer.

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