The synthesis of homochiral ligands based on [2.2]paracyclophane

Citations of this article
Mendeley users who have this article in their library.
Get full text


A new ortho-lithiation of homochiral 4-N,N-diethylamido[2.2]paracyclophane 8 is the key to the production of a wide variety of 4,5-disubstituted homochiral ligands. ψ-Geminal bromination of 8 proceeds in high yields and the resulting bromide may be converted into a variety of 4,13-disubstituted ligands. The o-lithiation and ψ-geminal reactions can be used sequentially to give 4,5,12-trisubstituted compounds in which two liganding groups have the same geometrical relationship as in 'Phanephos'™. Homochiral oxazolines with only planar chirality have been made, one of which has been shown to be an effective catalyst for the Heck reaction. © 2001 Elsevier Science Ltd. All rights reserved.




Pelter, A., Mootoo, B., Maxwell, A., & Reid, A. (2001). The synthesis of homochiral ligands based on [2.2]paracyclophane. Tetrahedron Letters, 42(47), 8391–8394.

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free