The synthesis of homochiral ligands based on [2.2]paracyclophane

  • Pelter A
  • Mootoo B
  • Maxwell A
 et al. 
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Abstract

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.

Author-supplied keywords

  • Homochiral ligands
  • Ortho-lithiation
  • [2.2]Paracyclophane
  • ψ-geminal substitution

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Authors

  • Andrew Pelter

  • Baldwin Mootoo

  • Anderson Maxwell

  • Alicia Reid

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