The synthesis of homochiral ligands based on [2.2]paracyclophane

✍ Scribed by Andrew Pelter; Baldwin Mootoo; Anderson Maxwell; Alicia Reid

• Book ID: 104231855
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 140 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01808-1

✦ Synopsis

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. c-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 c-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.