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

✍ Scribed by Michael Kreis; Christian J. Friedmann; Stefan Bräse

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
169 KB
Volume
11
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

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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