Diastereoselective Hartwig–Buchwald Reaction of Chiral Amines with  rac ‐[2.2]Paracyclophane Derivatives | Zendy

Kreis Michael | Zendy; Friedmann Christian J. | Zendy; Bräse Stefan | Zendy

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Diastereoselective Hartwig–Buchwald Reaction of Chiral Amines with rac ‐[2.2]Paracyclophane Derivatives

Author(s) -

Kreis Michael,

Friedmann Christian J.,

Bräse Stefan

Publication year - 2005

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.200500386

Subject(s) - amine gas treating , halide , chemistry , kinetic resolution , organic chemistry , cyclic amines , cyclophane , combinatorial chemistry , medicinal chemistry , catalysis , molecule , enantioselective synthesis

A Hartwig–Buchwald addition of a variety of chiral amines to rac ‐4‐bromo‐[2.2]paracyclophane and rac ‐trifluoromethanesulfonic acid (4‐[2.2]paracyclophane) ester was performed with high diastereoselectivities. Kinetic racemic resolution of the starting materials was achieved, providing a rapid access to enantiomerically enriched 4‐bromo‐[2.2]paracyclophane and the corresponding enantiomerically pure [2.2]paracyclophane amines. Additionally, the first reaction of a secondary amine with a [2.2]paracyclophane halide was achieved.

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