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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.